Electrophotographic photoreceptor with azo-containing photosensitive member

ABSTRACT

An electrophotographic photosensitive member having a photesensitive layer containing an azo compound represented by the following Formula [I], 
     Formula [I] ##STR1## wherein Y 1 , Y 2 , Y 3  and Y 4  each is a hydrogen atom, an alkyl group, an alkoxy group or a halogen atom; A 1  and A 2  each represents ##STR2## wherein Z is a group of atoms necessary to complete a substituted or unsubstituted aromatic carbocyclic ring of a substituted or unsubstituted aromatic heterocyclic ring; Q 3  is substituted or unsubstituted carbamoyl group or a substituted or unsubstituted sulfamoyl group; R 1  is a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted carbamoyl group, a carboxyl group, a carboxyl group or ester group thereof, or a cyano group; A&#39; is a substituted or unsubstituted aryl group; and R 2  and R 3  each is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryl group.

BACKGROUND OF THE INVENTION

The present invention relates to a photoreceptor, and more particularlyto a novel photoreceptor having a photosensitive layer comprising aspecific azo compound.

Those which have hitherto been widely used as the photoreceptor in theelectrophotographic process are inorganic photoreceptors having aphotosensitive layer comprised principally of an inorganicphotoconductive compound such as selenium, zinc oxide, cadmium sulfide,silicon, or the like. These, however, are not necessarily satisfactoryin the sensitivity, thermal stability, moisture resistance, durability,and the like. For example, selenium is difficult of manufacture because,when crystallized, its characteristics as of a photoreceptor becomesdeteriorated. And it tends to be crystallized due to the heat or fingermarks, whereby its property as of the photoreceptor becomesdeteriorated. Cadmium sulfide also is problematic in the moistureresistance as well as in the durability. And so is zinc oxide in thedurability.

For the purpose of overcoming such disadvantages of these inorganicphotoreceptors, the research and development of organic photoreceptorshaving a photosensitive layer comprised principally of any of variousorganic photoconductive compounds have become extensively carried on inrecent years. For example, Japanese Patent Examined Publication No.10496/1975 describes an organic photoreceptor having a photosensitivelayer containing both poly-N-vinylcarbazole and2,4,7-trinitro-9-fluorenone. This photoreceptor, however, is notnecessarily satisfactory in the sensitivity as well as in thedurability. In order to get rid of such shortcomings, attempts have beenmade to allot the carrier-generating function and carrier-transportfunction to different materials to thereby develop a higherperformance-having organic photoreceptor. Such a function-separated-typephotoreceptor permits a wide selection of appropriate materials for therespective functions thereof, and by using them any discretionalcharacteristic-having photoreceptors can be relatively easily produced.Thus, much research has been carried out for the development ofphotoreceptors of this type.

In the above-mentioned function-separated-type photoreceptors, as thecarrier-generating material thereof a variety of compounds have beenproposed. An example of those inorganic compounds usable as thecarrier-generating material is the amorphous selenium described in,e.g., Japanese Patent Examined Publication No. 16198/1968. This is to beused in combination with an organic photoconductive compound, but thecarrier-generating layer comprised of the amorphous selenium is stillnot improved to get rid of the disadvantage that the layer iscrystallized by heat to cause its characteristic to be deteriorated.

Also, there have been many proposals for electrophotographicphotoreceptors which use organic dyes or pigments as thecarrier-generating material. For example, those electrophotographicphotoreceptors which contain bisazo compounds in the photosensitivelayer thereof are already of the prior art found in Japanese PatentPublication Open to Public Inspection (hereinafter referred to asJapanese Patent O.P.I. Publication) Nos. 22834/1979, 73057/1980,117151/1980 and 46237/1981. These bisazo compounds, however, are notnecessarily satisfactory in the sensitivity, residual potential orstability against the repetitional use, and limits the selectable rangeof carrier-transport materials, and thus are unable to adequatelysatisfy diverse requirements in the electrophotographic process.

Further, in recent years, as the light source for the photoreceptor, gaslasers as Ar laser, He-Ne laser, etc., and semiconductor lasers havebegun to be used. These lasers are characterized by permitting theirtime-series ON/OFF operation, and are promising as the light source forthose image-processing function-having copiers including intelligentcopiers or for those output printers used for computers. Among otherthings, semiconductor lasers attract attention for the reason that theirnature requires no electric signal/light signal conversion elements suchas acoustic elements, and they enable making their devices to be of asmaller size and a lighter weight. However, not only is thesemiconductor laser's output lower than that of the gas laser but alsoits oscillating wavelength is on the longer wavelength side (not lessthan about 780 nm), and in contrast, the spectral sensitivity ofconventional photoreceptors is on the far shorter wavelength side thanthat of the semiconductor laser. Accordingly, conventionalphotoreceptors can not be used as the photoreceptor for which thesemiconductor laser is used as the light source.

It is therefore an object of the present invention to provide aphotoreceptor comprising a specific azo compound which is excellent inthe carrier-generating function.

It is another object of the present invention to provide a photoreceptorwhich is so excellently durable that it has a high sensitivity and smallresidual potential and, even when used repeatedly, these characteristicsare unchangeably stable.

It is a further object of the present invention to provide aphotoreceptor comprising an azo compound which, even when used incombination with any of diverse carrier-transport materials, is capableof acting effectively as a carrier-generating material.

It is still another object of the present invention to provide aphotoreceptor which has an adequately substantial sensitivity even whenused to a longer-wavelength light source such as a semiconductor laser.

A still further object of the present invention will become apparentfrom the description in this specification.

BRIEF DESCRIPTION OF THE DRAWINGS

FIGS. 1 through 6 are cross-sectional views showing examples of themechanical construction of the photoreceptor of the present invention.

DETAILED DESCRIPTION OF THE INVENTION

As a result of our continued investigation to accomplish the aboveobjects, we have now found that any one of those azo compounds havingthe following formula [I] is capable of acting as an effectiveconstituent of the photoreceptor, and thus, we have completed thisinvention.

Formula [I] ##STR3## wherein Y₁, Y₂, Y₃ and Y₄ each is a hydrogen atom,an alkyl group, an alkoxy group or a halogen atom; A₁ and A₂ each is##STR4## and Q₃ is a substituted or unsubstituted carbamoyl group##STR5## a substituted or unsubstituted sulfamoyl group ##STR6## whereinR₄ is a substituted or unsubstituted alkyl group having from 1 to 4carbon atoms, a substituted or unsubstituted aralkyl group or asubstituted or unsubstituted phenyl group; and R₅ is a hydrogen atom, asubstituted or unsubstituted alkyl group having from 1 to 4 carbonatoms, a substituted or unsubstituted aromatic carbocyclic group (suchas a substituted or unsubstituted phenyl group, a substituted orunsubstituted anthryl group, etc.), or a substituted or unsubstitutedaromatic heterocyclic group (such as a substituted or unsubstitutedcarbazolyl group, a substituted or unsubstituted dibenzofuryl group,etc.).

Those substituents to these groups include, e.g., alkyl groups (such asmethyl, ethyl, isopropyl, tertiary butyl, trifluoromethyl, etc.),substituted or unsubstituted aralkyl groups (such as benzyl, phenethyl,etc.), halogen atoms (chlorine, bromine, fluorine, iodine), substitutedor unsubstituted alkoxy groups having from 1 to 4 carbon atoms (such asmethoxy, ethoxy, isopropoxy, tertiary butoxy, 2-chloroethoxy, etc.),hydroxy group, substituted or unsubstituted aryloxy groups (such asp-chlorophenoxy, 1-napthoxy, etc.), aryloxy groups (such as acetyloxy,p-cyanobenzoyloxy, etc.), carboxy group and esters thereof (such asethoxycarbonyl, m-bromophenoxycarbonyl, etc.), substituted orunsubstituted carbamoyl groups (such as aminocarbonyl, tertiarybutylaminocarbonyl, anilinocarbonyl), acyl groups (such as acetyl,o-nitrobenzoyl), sulfo group, substituted or unsubstituted sulfamoylgroups (such as aminosulfonyl, tertiary butylaminosulfonyl,p-tolylaminosulfonyl), amino group, acylamino groups (such asacetylamino, benzoylamino, etc.), sulfonamido groups (such asmethanesulfonamido, p-toluenesulfonamido, etc.), cyano group, nitrogroup, and the like. The preferred substituents among these aresubstituted or unsubstituted alkyl groups having from 1 to 4 carbonatoms (such as methyl, ethyl, isopropyl, n-butyl, trifluoromethyl,etc.), halogen atoms (chlorine, bromine, fluorine, iodine), substitutedor unsubstituted alkoxy groups having from 1 to 4 carbon atoms (such asmethoxy, ethoxy, tertiary butoxy, 2-chloroethoxy, etc.), cyano group andnitro group.

Z is a group of atoms necessary to form a substituted or unsubstitutedaromatic carbocyclic ring or a substituted or unsubstituted aromaticheterocyclic ring, and concretely it represents a group of atoms for theformation of, e.g., a substituted or unsubstituted benzene ring, asubstituted or unsubstituted naphthalene ring, a substituted orunsubstituted indole ring, or a substituted or unsubstituted carbazolering.

Those substituents to these rings include, e.g., a series of thesubstituents enumerated as those of R₄ and R₅, and preferably halogenatoms (chlorine, bromine, fluorine, iodine), sulfo group, and sulfamoylgroups (such as aminosulfonyl, p-tolylaminosulfonyl, etc.).

R₁ is a hydrogen atom, a substituted or unsubstituted alkyl group, asubstituted or unsubstituted amino group, a carboxyl group or esterthereof, a substituted or unsubstituted carbamoyl group, or a cyanogroup, and preferably a hydrogen atom, a substituted or unsubstitutedalkyl group having from 1 to 4 carbon atoms (such as methyl, ethyl,isopropyl, tertiary butyl, trilfuoromethyl, etc.), or a cyano group.

A' is a substituted or unsubstituted aryl group, and preferably asubstituted or unsubstituted phenyl group. Those substituents to thesegroups include, e.g., a series of the substituents enumerated as thoseof R₄ and R₅, and preferably halogen atoms (chlorine, bromine, fluorine,iodine), substituted or unsubstituted alkyl groups having from 1 to 4carbon atoms (such as methyl, ethyl, isopropyl, tertiary butyl,trifluoromethyl, etc.), and substituted or unsubstituted alkoxy groupshaving from 1 to 4 carbon atoms (such as methoxy, ethoxy, isopropoxy,tertiary butoxy, 2-chloroethoxy).

R₂ and R₃ each is a substituted or unsubstituted alkyl group, asubstituted or unsubstituted aralkyl group, or substituted orunsubstituted aryl group, and preferably a substituted or unsubstitutedalkyl group having from 1 to 4 carbon atoms (such as methyl, ethyl,isopropyl, tertiary butyl, trifluoromethyl, etc.) or a substituted orunsubstituted phenyl group (such as phenyl, p-methoxyphenyl,m-chlorophenyl, etc.).

Examples of the useful azo compounds having Formula [I] in thisinvention include those having, e.g., the following structural formulas,but the azo compounds of this invention are not limited to and by theexamples.

Exemplified Compounds Formula [II]

    __________________________________________________________________________     ##STR7##                                                                     Compound                                                                      No.    Y.sub.4                                                                            Y.sub.3                                                                           Y.sub.2                                                                           Y.sub.1                                                                           R.sub.6                                                                            R.sub.7                                                                            R.sub.8                                                                             R.sub.9                                                                            R.sub.10                         __________________________________________________________________________    A-1    H    H   H   H   H    H    H     H    H                                A-2    H    H   H   H   CH.sub.3                                                                           H    H     H    H                                A-3    H    H   H   H   CH.sub. 3                                                                          H    CH.sub.3                                                                            H    H                                A-4    H    H   H   H   C.sub.2 H.sub.5                                                                    H    H     H    H                                A-5    H    H   H   H   H    H    OCH.sub.3                                                                           H    H                                A-6    H    H   H   H   H    OCH.sub.3                                                                          OCH.sub.3                                                                           H    H                                A-7    H    H   H   H   CH.sub.3                                                                           H    OCH.sub.3                                                                           H    H                                A-8    H    H   H   H   Cl   H    H     H    H                                A-9    H    H   H   H   Br   H    H     H    H                                A-10   H    H   H   H   F    H    H     H    H                                A-11   H    H   H   H   Cl   Cl   H     H    H                                A-12   H    H   H   H   Cl   H    Cl    H    H                                A-13   H    H   H   H   H    Cl   Cl    H    H                                A-14   H    H   H   H   Cl   H    Cl    H    H                                A-15   H    H   H   H   H    Cl   H     Cl   H                                A-16   H    H   H   H   H    CH.sub.3                                                                           H     H    H                                A-17   H    H   H   H   H    H    CH.sub.3                                                                            H    H                                A-18   H    H   H   H   H    H    CH.sub.3                                                                            CH.sub.3                                                                           H                                A-19   H    H   H   H   H    CH.sub.3                                                                           H     CH.sub.3                                                                           H                                A-20   H    H   H   H   H    C.sub.2 H.sub.5                                                                    H     H    H                                A-21   H    H   H   H   H    H    C.sub.2 H.sub.5                                                                     H    H                                A-22   H    H   H   H   H    H    F     H    H                                A-23   H    H   H   H   H    F    H     H    H                                A-24   H    H   H   H   H    H    Br    H    H                                A-25   H    H   H   H   H    OCH.sub.3                                                                          OCH.sub.3                                                                           OCH.sub.3                                                                          H                                A-26   H    H   H   H   OCH.sub.3                                                                          H    H     H    H                                A-27   H    H   H   H   H    H    C.sub.8 H.sub.17                                                                    H    H                                A-28   H    H   H   H   H    H    COCH.sub.3                                                                          H    H                                A-29   H    H   H   H   H    OH   H     H    H                                A-30   H    H   H   H   H    NO.sub.2                                                                           H     H    H                                A-31   H    H   H   H   C.sub.4 H.sub.9                                                                    H    H     H    H                                A-32   H    H   H   H   H    H    C.sub.4 H.sub.9                                                                     H    H                                A-33   H    H   H   H   H    H    C.sub.3 H.sub.7                                                                     H    H                                A-34   H    H   H   H   H    H    I     H    H                                A-35   CH.sub.3                                                                           H   H   H   H    H    H     H    H                                A-36   CH.sub.3                                                                           H   H   H   CH.sub.3                                                                           H    H     H    H                                A-37   CH.sub.3                                                                           H   H   H   H    CH.sub.3                                                                           H     H    H                                A-38   CH.sub.3                                                                           H   H   H   H    H    CH.sub.3                                                                            H    H                                A-39   CH.sub.3                                                                           H   H   H   H    H    H     CH.sub.3                                                                           H                                A-40   CH.sub.3                                                                           H   H   H   H    CH.sub.3                                                                           H     CH.sub.3                                                                           H                                A-41   CH.sub.3                                                                           H   H   H   CH.sub.3                                                                           H    CH.sub.3                                                                            H    H                                A-42   CH.sub.3                                                                           H   H   H   CH.sub.3                                                                           H    OCH.sub.3                                                                           H    H                                A-43   CH.sub.3                                                                           H   H   H   H    H    OCH.sub.3                                                                           H    H                                A-44   CH.sub.3                                                                           H   H   H   C.sub.2 H.sub.5                                                                    H    H     H    H                                A-45   CH.sub.3                                                                           H   H   H   C.sub.2 H.sub.5                                                                    H    C.sub.2 H.sub.5                                                                     H    H                                A-46   OCH.sub.3                                                                          H   H   H   H    H    H     H    H                                A-47   OCH.sub.3                                                                          H   H   H   H    H    Cl    H    H                                A-48   OCH.sub.3                                                                          H   H   H   CH.sub.3                                                                           H    H     H    H                                __________________________________________________________________________

Formula [III]

    __________________________________________________________________________     ##STR8##                                                                     Compound                                                                      No.    Y.sub.4                                                                            Y.sub.3                                                                           Y.sub.2                                                                           Y.sub.1                                                                           R.sub.6                                                                            R.sub.7                                                                            R.sub.8                                                                            R.sub.9                                                                            R.sub.10                          __________________________________________________________________________    A-49   H    H   H   H   H    H    H    H    H                                 A-50   H    H   H   H   CH.sub.3                                                                           H    H    H    H                                 A-51   H    H   H   H   CH.sub. 3                                                                          H    CH.sub.3                                                                           H    H                                 A-52   H    H   H   H   C.sub.2 H.sub.5                                                                    H    H    H    H                                 A-53   H    H   H   H   H    H    OCH.sub.3                                                                          H    H                                 A-54   H    H   H   H   H    OCH.sub.3                                                                          OCH.sub.3                                                                          H    H                                 A-55   H    H   H   H   CH.sub.3                                                                           H    OCH.sub.3                                                                          H    H                                 A-56   H    H   H   H   Cl   H    H    H    H                                 A-57   H    H   H   H   Br   H    H    H    H                                 A-58   H    H   H   H   F    H    H    H    H                                 A-59   H    H   H   H   Cl   Cl   H    H    H                                 A-60   H    H   H   H   Cl   H    Cl   H    H                                 A-61   H    H   H   H   H    Cl   Cl   H    H                                 A-62   H    H   H   H   Cl   H    Cl   H    H                                 A-63   H    H   H   H   H    Cl   H    Cl   H                                 A-64   H    H   H   H   H    CH.sub.3                                                                           H    H    H                                 A-65   H    H   H   H   H    H    CH.sub.3                                                                           H    H                                 A-66   H    H   H   H   H    H    CH.sub.3                                                                           CH.sub.3                                                                           H                                 A-67   H    H   H   H   H    CH.sub.3                                                                           H    CH.sub.3                                                                           H                                 A-68   H    H   H   H   H    C.sub.2 H.sub.5                                                                    H    H    H                                 A-69   H    H   H   H   H    H    C.sub. 2 H.sub.5                                                                   H    H                                 A-70   H    H   H   H   H    H    F    H    H                                 A-71   H    H   H   H   H    F    H    H    H                                 A-72   H    H   H   H   H    H    Br   H    H                                 A-73   H    H   H   H   H    OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                                                          H                                 A-74   H    H   H   H   OCH.sub.3                                                                          H    H    H    H                                 A-75   H    H   H   H   H    H    C.sub.8 H.sub.17                                                                   H    H                                 A-76   H    H   H   H   H    H    OCH.sub.3                                                                          H    H                                 A-77   H    H   H   H   H    OH   H    H    H                                 A-78   H    H   H   H   H    NO.sub.2                                                                           H    H    H                                 A-79   H    H   H   H   C.sub.4 H.sub.9                                                                    H    H    H    H                                 A-80   H    H   H   H   H    H    C.sub.4 H.sub.9                                                                    H    H                                 A-81   H    H   H   H   H    H    C.sub.3 H.sub.7                                                                    H    H                                 A-82   H    H   H   H   H    H    I    H    H                                 A-83   CH.sub.3                                                                           H   H   H   H    H    H    H    H                                 A-84   CH.sub.3                                                                           H   H   H   CH.sub.3                                                                           H    H    H    H                                 A-85   CH.sub.3                                                                           H   H   H   H    CH.sub.3                                                                           H    H    H                                 A-86   CH.sub.3                                                                           H   H   H   H    H    CH.sub.3                                                                           H    H                                 A-87   CH.sub.3                                                                           H   H   H   H    H    H    CH.sub.3                                                                           H                                 A-88   CH.sub.3                                                                           H   H   H   H    CH.sub.3                                                                           H    CH.sub.3                                                                           H                                 A-89   CH.sub.3                                                                           H   H   H   CH.sub.3                                                                           H    CH.sub.3                                                                           H    H                                 A-90   CH.sub.3                                                                           H   H   H   CH.sub.3                                                                           H    OCH.sub.3                                                                          H    H                                 A-91   CH.sub.3                                                                           H   H   H   H    H    OCH.sub.3                                                                          H    H                                 A-92   CH.sub.3                                                                           H   H   H   C.sub.2 H.sub.5                                                                    H    H    H    H                                 A-93   CH.sub.3                                                                           H   H   H   C.sub.2 H.sub.5                                                                    H    C.sub.2 H.sub.5                                                                    H    H                                 A-94   OCH.sub.3                                                                          H   H   H   H    H    H    H    H                                 A-95   OCH.sub.3                                                                          H   H   H   H    H    Cl   H    H                                 A-96   OCH.sub.3                                                                          H   H   H   CH.sub.3                                                                           H    H    H    H                                 __________________________________________________________________________

Formula [IV]

    __________________________________________________________________________     ##STR9##                                                                     Compound                                                                      No.    Y.sub.4                                                                            Y.sub.3                                                                           Y.sub.2                                                                           Y.sub.1                                                                           R.sub.6                                                                             R.sub.7                                                                            R.sub.8                                                                             R.sub.9                                                                            R.sub.10                        __________________________________________________________________________    A-97   H    H   H   H   H     H    H     H    H                               A-98   H    H   H   H   CH.sub.3                                                                            H    H     H    H                               A-99   H    H   H   H   CH.sub.3                                                                            H    CH.sub.3                                                                            H    H                               A-100  H    H   H   H   C.sub.2 H.sub.5                                                                     H    H     H    H                               A-101  H    H   H   H   H     H    OCH.sub.3                                                                           H    H                               A-102  H    H   H   H   H     OCH.sub.3                                                                          OCH.sub.3                                                                           H    H                               A-103  H    H   H   H   CH.sub.3                                                                            H    OCH.sub.3                                                                           H    H                               A-104  H    H   H   H   Cl    H    H     H    H                               A-105  H    H   H   H   Br    H    H     H    H                               A-106  H    H   H   H   F     H    H     H    H                               A-107  H    H   H   H   Cl    Cl   H     H    H                               A-108  H    H   H   H   Cl    H    Cl    H    H                               A-109  H    H   H   H   H     Cl   Cl    H    H                               A-110  H    H   H   H   Cl    H    Cl    H    H                               A-111  H    H   H   H   H     Cl   H     Cl   H                               A-112  H    H   H   H   H     CH.sub.3                                                                           H     H    H                               A-113  H    H   H   H   H     H    CH.sub.3                                                                            H    H                               A-114  H    H   H   H   H     H    CH.sub.3                                                                            CH.sub.3                                                                           H                               A-115  H    H   H   H   H     CH.sub.3                                                                           H     CH.sub.3                                                                           H                               A-116  H    H   H   H   H     C.sub.2 H.sub.5                                                                    H     H    H                               A-117  H    H   H   H   H     H    C.sub.2 H.sub.5                                                                     H    H                               A-118  H    H   H   H   H     H    F     H    H                               A-119  H    H   H   H   H     F    H     H    H                               A-120  H    H   H   H   H     H    Br    H    H                               A-121  H    H   H   H   H     OCH.sub.3                                                                          OCH.sub.3                                                                           OCH.sub.3                                                                          H                               A-122  H    H   H   H   OCH.sub.3                                                                           H    H     H    H                               A-123  H    H   H   H   H     H    C.sub.8 H.sub.17                                                                    H    H                               A-124  H    H   H   H   H     H    OCH.sub.3                                                                           H    H                               A-125  H    H   H   H   H     OH   H     H    H                               A-126  H    H   H   H   H     NO.sub.2                                                                           H     H    H                               A-127  H    H   H   H   C.sub.4 H.sub.9                                                                     H    H     H    H                               A-128  H    H   H   H   H     H    C.sub.4 H.sub.9                                                                     H    H                               A-129  H    H   H   H   H     H    C.sub.3 H.sub.7                                                                     H    H                               A-130  H    H   H   H   H     H    I     H    H                               A-131  CH.sub.3                                                                           H   H   H   H     H    H     H    H                               A-132  CH.sub.3                                                                           H   H   H   CH.sub.3                                                                            H    H     H    H                               A-133  CH.sub. 3                                                                          H   H   H   H     CH.sub.3                                                                           H     H    H                               A-134  CH.sub.3                                                                           H   H   H   H     H    CH.sub.3                                                                            H    H                               A-135  CH.sub.3                                                                           H   H   H   H     H    H     CH.sub.3                                                                           H                               A-136  CH.sub.3                                                                           H   H   H   H     CH.sub.3                                                                           H     CH.sub.3                                                                           H                               A-137  CH.sub.3                                                                           H   H   H   CH.sub.3                                                                            H    CH.sub.3                                                                            H    H                               A-138  CH.sub.3                                                                           H   H   H   CH.sub.3                                                                            H    OCH.sub.3                                                                           H    H                               A-139  CH.sub.3                                                                           H   H   H   H     H    OCH.sub.3                                                                           H    H                               A-140  CH.sub.3                                                                           H   H   H   C.sub.2 H.sub.5                                                                     H    H     H    H                               A-141  CH.sub.3                                                                           H   H   H   C.sub.2 H.sub.5                                                                     H    C.sub.2 H.sub.5                                                                     H    H                               A-142  OCH.sub.3                                                                          H   H   H   H     H    H     H    H                               A-143  OCH.sub.3                                                                          H   H   H   H     H    Cl    H    H                               A-144  OCH.sub.3                                                                          H   H   H   CH.sub.3                                                                            H    H     H    H                               __________________________________________________________________________

Formula [V]

    __________________________________________________________________________     ##STR10##                                                                    Compound                                                                      No.    Y.sub.4                                                                            Y.sub.3                                                                          Y.sub.2                                                                          Y.sub.1                                                                           R.sub.6                                                                           R.sub.7                                                                            R.sub.8                                                                             R.sub.9                                                                             R.sub.10                           __________________________________________________________________________    A-145  H    H  H  H   H    H   H     H     H                                  A-146  H    H  H  H   CH.sub.3                                                                          H    H     H     H                                  A-147  H    H  H  H   CH.sub.3                                                                          H    CH.sub.3                                                                            H     H                                  A-148  H    H  H  H   C.sub.2 H.sub.5                                                                   H    H     H     H                                  A-149  H    H  H  H   H   H    OCH.sub.3                                                                           H     H                                  A-150  H    H  H  H   H   OCH.sub.3                                                                          OCH.sub.3                                                                           H     H                                  A-151  H    H  H  H   CH.sub.3                                                                          H    OCH.sub.3                                                                           H     H                                  A-152  H    H  H  H   Cl  H    H     H     H                                  A-153  H    H  H  H   Br  H    H     H     H                                  A-154  H    H  H  H   F   H    H     H     H                                  A-155  H    H  H  H   Cl  Cl   H     H     H                                  A-156  H    H  H  H   Cl  H    Cl    H     H                                  A-157  H    H  H  H   H   Cl   Cl    H     H                                  A-158  H    H  H  H   Cl  H    Cl    H     H                                  A-159  H    H  H  H   H   Cl   H     Cl    H                                  A-160  H    H  H  H   H   CH.sub.3                                                                           H     H     H                                  A-161  H    H  H  H   H   H    CH.sub.3                                                                            H     H                                  A-162  H    H  H  H   H   H    CH.sub.3                                                                            CH.sub.3                                                                            H                                  A-163  H    H  H  H   H   Cl   H     CH.sub.3                                                                            H                                  A-164  H    H  H  H   H   C.sub.2 H.sub.5                                                                    H     H     H                                  A-165  H    H  H  H   H   H    C.sub.2 H.sub.5                                                                     H     H                                  A-166  H    H  H  H   H   H    F     H     H                                  A-167  H    H  H  H   H   F    H     H     H                                  A-168  H    H  H  H   H   H    Br    H     H                                  A-169  H    H  H  H   H   OCH.sub.3                                                                          OCH.sub.3                                                                           OCH.sub.3                                                                           H                                  A-170  H    H  H  H   OCH.sub.3                                                                         H    H     H     H                                  A-171  H    H  H  H   H   H    C.sub.8 H.sub.17                                                                    H     H                                  A-172  H    H  H  H   H   H    OCH.sub.3                                                                           H     H                                  A-173  H    H  H  H   H   OH   H     H     H                                  A-174  H    H  H  H   H   NO.sub.2                                                                           H     H     H                                  A-175  H    H  H  H   C.sub.4 H.sub.9                                                                   H    H     H     H                                  A-176  H    H  H  H   H   H    C.sub.4 H.sub.9                                                                     H     H                                  A-177  H    H  H  H   H   H    C.sub.3 H.sub.7                                                                     H     H                                  A-178  H    H  H  H   H   H    I     H     H                                  A-179  CH.sub.3                                                                           H  H  H   H   H    H     H     H                                  A-180  CH.sub.3                                                                           H  H  H   CH.sub.3                                                                          H    H     H     H                                  A-181  CH.sub.3                                                                           H  H  H   H   CH.sub.3                                                                           H     H     H                                  A-182  CH.sub.3                                                                           H  H  H   H   H    CH.sub.3                                                                            H     H                                  A-183  CH.sub.3                                                                           H  H  H   H   H    H     CH.sub.3                                                                            H                                  A-184  CH.sub.3                                                                           H  H  H   H   CH.sub.3                                                                           H     CH.sub.3                                                                            H                                  A-185  CH.sub.3                                                                           H  H  H   CH.sub.3                                                                          H    CH.sub.3                                                                            H     H                                  A-186  CH.sub.3                                                                           H  H  H   CH.sub.3                                                                          H    OCH.sub.3                                                                           H     H                                  A-187  CH.sub.3                                                                           H  H  H   H   H    OCH.sub.3                                                                           H     H                                  A-188  CH.sub.3                                                                           H  H  H   C.sub.2 H.sub.5                                                                   H    H     H     H                                  A-189  CH.sub.3                                                                           H  H  H   C.sub.2 H.sub.5                                                                   H    C.sub.2 H.sub.5                                                                     H     H                                  A-190  OCH.sub.3                                                                          H  H  H   H   H    H     H     H                                  A-191  OCH.sub.3                                                                          H  H  H   H   H    Cl    H     H                                  A-192  OCH.sub.3                                                                          H  H  H   CH.sub.3                                                                          H    H     H     H                                  __________________________________________________________________________

Formula [VI]

    __________________________________________________________________________     ##STR11##                                                                    Compound                                                                      No.   Y.sub.4                                                                           R.sub.6                                                                           R.sub.7                                                                          R.sub.8                                                                           R.sub.9                                                                          R.sub.10                                                                          R.sub.11                                                                          R.sub.12                                                                           R.sub.13                                                                           R.sub.14                                                                          R.sub.15                        __________________________________________________________________________    A-193 H   H   H  H   H  H   H   H    H    H   H                               A-194 H   CH.sub.3                                                                          H  H   H  H   H   H    H    H   H                               A-195 H   CH.sub.3                                                                          H  H   H  H   CH.sub.3                                                                          H    H    H   H                               A-196 H   CH.sub.3                                                                          H  CH.sub.3                                                                          H  H   CH.sub.3                                                                          H    CH.sub.3                                                                           H   H                               A-197 H   H   H  H   H  H   CH.sub.3                                                                          H    H    H   H                               A-198 H   H   H  OCH.sub.3                                                                         H  H   H   H    H    H   H                               A-199 H   H   H  OCH.sub.3                                                                         H  H   H   H    OCH.sub.3                                                                          H   H                               A-200 H   H   H  H   H  H   H   H    OCH.sub.3                                                                          H   H                               A-201 H   H   H  CH.sub.3                                                                          H  H   H   H    CH.sub.3                                                                           H   H                               A-202 H   CH.sub.3                                                                          H  OCH.sub.3                                                                         H  H   H   H    H    H   H                               A-203 H   CH.sub.3                                                                          H  OCH.sub.3                                                                         H  H   CH.sub.3                                                                          H    OCH.sub.3                                                                          H   H                               A-204 H   H   H  H   H  H   Cl  H    H    H   H                               A-205 H   H   H  H   H  H   H   H    Cl   H   H                               A-206 H   H   H  Cl  H  H   H   H    Cl   H   H                               A-207 H   H   H  H   H  H   H   H    Br   H   H                               A-208 H   H   H  Br  H  H   H   H    H    H   H                               A-209 H   H   H  Br  H  H   H   H    Br   H   H                               A-210 H   H   H  H   H  H   Br  H    H    H   H                               A-211 H   C.sub.2 H.sub.5                                                                   H  H   H  H   H   H    H    H   H                               A-212 H   C.sub.2 H.sub.5                                                                   H  H   H  H   C.sub.2 H.sub.5                                                                   H    H    H   H                               A-213 H   C.sub.2 H.sub.5                                                                   H  H   H  H   Cl  H    H    H   H                               A-214 H   C.sub.2 H.sub.5                                                                   H  H   H  H   CH.sub.3                                                                          H    H    H   H                               A-215 H   H   H  OCH.sub.3                                                                         H  H   H   H    Cl   H   H                               A-216 H   H   H  OCH.sub.3                                                                         H  H   H   H    Br   H   H                               A-217 H   H   H  OCH.sub.3                                                                         H  H   CH.sub.3                                                                          H    CH.sub.3                                                                           H   H                               A-218 H   H   H  OCH.sub.3                                                                         H  H   H   H    C.sub.2 H.sub.5                                                                    H   H                               A-219 H   CH.sub.3                                                                          H  OCH.sub.3                                                                         H  H   Cl  H    H    H   H                               A-220 H   CH.sub.3                                                                          H  OCH.sub.3                                                                         H  H   H   H    Cl   H   H                               A-221 H   CH.sub.3                                                                          H  OCH.sub.3                                                                         H  H   H   H    Br   H   H                               A-222 H   CH.sub.3                                                                          H  OCH.sub.3                                                                         H  H   H   CH.sub.3                                                                           H    H   H                               A-223 H   CH.sub.3                                                                          H  OCH.sub.3                                                                         H  H   H   OCH.sub.3                                                                          H    H   H                               A-224 H   CH.sub.3                                                                          H  OCH.sub.3                                                                         H  H   H   H    C.sub.2 H.sub.5                                                                    H   H                               A-225 H   CH.sub.3                                                                          H  OCH.sub.3                                                                         H  H   H   H    C.sub.4 H.sub.9                                                                    H   H                               A-226 H   H   H  OCH.sub.3                                                                         H  H   Cl  H    H    H   H                               A-227 H   H   H  OCH.sub.3                                                                         H  H   Br  H    H    H   H                               A-228 CH.sub.3                                                                          H   H  H   H  H   H   H    H    H   H                               __________________________________________________________________________

Formula [VII]

    __________________________________________________________________________     ##STR12##                                                                    Compound                                                                      No.   Y.sub.3                                                                          R.sub.6                                                                           R.sub.7                                                                          R.sub.8                                                                            R.sub.9                                                                          R.sub.10                                                                          R.sub.11                                                                           R.sub.12                                                                             R.sub.13                                                                           R.sub.14                                                                           R.sub.15                    __________________________________________________________________________    A-229 H  H   H  H    H  H   H    H      H    H    H                           A-230 H  CH.sub.3                                                                          H  H    H  H   H    H      H    H    H                           A-231 H  CH.sub.3                                                                          H  H    H  H   CH.sub.3                                                                           H      H    H    H                           A-232 H  CH.sub.3                                                                          H  CH.sub.3                                                                           H  H   CH.sub.3                                                                           H      CH.sub.3                                                                           H    H                           A-233 H  H   H  H    H  H   CH.sub.3                                                                           H      H    H    H                           A-234 H  H   H  OCH.sub.3                                                                          H  H   H    H      H    H    H                           A-235 H  H   H  OCH.sub.3                                                                          H  H   H    H      OCH.sub.3                                                                          H    H                           A-236 H  H   H  H    H  H   H    H      OCH.sub.3                                                                          H    H                           A-237 H  H   H  CH.sub.3                                                                           H  H   H    H      CH.sub.3                                                                           H    H                           A-238 H  CH.sub.3                                                                          H  OCH.sub.3                                                                          H  H   H    H      H    H    H                           A-239 H  CH.sub.3                                                                          H  OCH.sub.3                                                                          H  H   CH.sub.3                                                                           H      OCH.sub.3                                                                          H    H                           A-240 H  H   H  H    H  H   Cl   H      H    H    H                           A-241 H  H   H  H    H  H   H    H      Cl   H    H                           A-242 H  H   H  Cl   H  H   H    H      Cl   H    H                           A-243 H  H   H  H    H  H   H    H      Br   H    H                           A-244 H  H   H  Br   H  H   H    H      H    H    H                           A-245 H  H   H  Br   H  H   H    H      Br   H    H                           A-246 H  H   H  H    H  H   Br   H      H    H    H                           A-247 H  C.sub.2 H.sub.5                                                                   H  H    H  H   H    H      H    H    H                           A-248 H  C.sub.2 H.sub.5                                                                   H  H    H  H   C.sub.2 H.sub.5                                                                    H      H    H    H                           A-249 H  C.sub.2 H.sub.5                                                                   H  H    H  H   Cl   H      H    H    H                           A-250 H  C.sub.2 H.sub.5                                                                   H  H    H  H   CH.sub.3                                                                           H      H    H    H                           A-251 H  H   H  OCH.sub.3                                                                          H  H   H    H      Cl   H    H                           A-252 H  H   H  OCH.sub.3                                                                          H  H   H    H      Br   H    H                           A-253 H  H   H  OCH.sub.3                                                                          H  H   CH.sub.3                                                                           H      CH.sub.3                                                                           H    H                           A-254 H  H   H  OCH.sub.3                                                                          H  H   H    H      C.sub.2 H.sub.5                                                                    H    H                           A-255 H  CH.sub.3                                                                          H  OCH.sub.3                                                                          H  H   Cl   H      H    H    H                           A-256 H  CH.sub.3                                                                          H  OCH.sub.3                                                                          H  H   H    H      Cl   H    H                           A-257 H  CH.sub.3                                                                          H  OCH.sub.3                                                                          H  H   H    H      Br   H    H                           A-258 H  CH.sub.3                                                                          H  OCH.sub.3                                                                          H  H   H    CH.sub.3                                                                             H    H    H                           A-259 H  CH.sub.3                                                                          H  OCH.sub. 3                                                                         H  H   H    OCH.sub.3                                                                            H    H    H                           A-260 H  CH.sub.3                                                                          H  OCH.sub.3                                                                          H  H   H    H      C.sub.2 H.sub.5                                                                    H    H                           A-261 H  CH.sub.3                                                                          H  OCH.sub.3                                                                          H  H   H    H      C.sub.4 H.sub.9                                                                    H    H                           A-262 H  H   H  OCH.sub.3                                                                          H  H   Cl   H      H    H    H                           A-263 H  H   H  OCH.sub.3                                                                          H  H   Br   H      H    H    H                           A-264 H  H   H  H    H  H   H    H      H    H    H                           A-265                                                                                ##STR13##                                                              A-266                                                                                ##STR14##                                                              A-267                                                                                ##STR15##                                                              A-268                                                                                ##STR16##                                                              A-269                                                                                ##STR17##                                                              A-270                                                                                ##STR18##                                                              __________________________________________________________________________

Any of the above-enumerated azo compounds may be easily synthesized inknown manners. An example of the synthesis is given below:

(Synthesis of Exemplified Compound A-3)

Twenty milliliters of 47% HBF₄ are put in a 100 ml flask, and to this,with stirring at -5° C., are added dropwise 8 ml of an aqueous solutioncontaining 2.8 g (0.04 mole) of NaNO₂, and at the same time is slowlyadded a liquid prepared by dispersing 3.6 g (0.02 mole) ofp-phenylenediamine hydrochloride into 6 ml of water. After completion ofthe addition, the reaction liquid is stirred for 15 minutes at the sametemperature, and then the deposited crystals are filtered. The obtainedtetrazonium salt is dissolved into 400 ml of cold DMF, and the solutionis kept at a temperature of not more than 5° C.

On the other hand, a solution of 14.0 g (0.048 mole) of2',4'-dimethyl-2-hydroxy-3-naphthoic acid anilide dissolved in 700 ml ofDMF is cooled and added to the above-prepared tetrazonium salt solution.To this mixture, with stirring, is added dropwise a solution, kept atnot more than 5° C., of 10.8 g of CH₃ COONa.3H₂ O dissolved in 50 ml ofwater. After the dropping, the liquid is further stirred for two hoursat the same temperature, and the resulting deposit is filtered. Thefiltrated deposit is washed with DMF, with water, and then withmethanol, and then dried, whereby 6.78 g (yield 43%) of ExemplifiedCompound A-3 are obtained.

Any of the foregoing azo compounds of this invention has an excellentphotoconductivity. The production of a photoreceptor with use of thecompound may be made by providing on a conductive support aphotosensitive layer of the azo compound of this invention dispersed ina binder, but particularly excellent results can be obtained in the casewhere the azo compound of this invention, making the most of itsphotoconductivity, especially its carrier-generating ability, is used asa carrier-generating material, and also a carrier-transport materialwhich can effectively act in combination therewith is used, thusconstructing a so-called function-separated-type photoreceptor. Thefunction-separated-type photoreceptor is allowed to be of the dispersiontype, but more desirable to be of the multilayer type comprising acarrier-generating layer containing a carrier-generating material and acarrier-transport layer containing a carrier-transport material.

As for the mechanical construction of a photoreceptor, various forms areknown. The photoreceptor of this invention is allowed to take any of theforms.

Usually, such forms as shown in FIGS. 1 through 6 are applicable. InFIGS. 1 and 3, on a conductive support 1 is provided a photosensitivelayer 4 in the multi-layer form comprising a carrier-generating layer 2consisting principally of the foregoing azo compound and acarrier-transport layer 3 consisting principally of a carrier-transportmaterial.

As is indicated in FIGS. 3 and 4, photosensitive layer 4 may also beprovided through an interlayer 5 on the conductive support. Whenphotosensitive layer 4 is of the double construction like this, the mostexcellent electrophotographic characteristic-having photoreceptor can beobtained. Also, in this invention, as is shown in FIGS. 5 and 6,photosensitive layer 4 comprising carrier-generating material 7dispersed in layer 6 consisting principally of a carrier-transportmaterial may be directly or through interlayer 5 on conductive support1.

In the case where the azo compound of this invention is used as acarrier-generating material, the carrier-transport material usable incombination with this includes electronacceptors tending to transportelectrons such as trinitrofluorenone, tetranitrofluorenone, etc., andelectron donative materials tending to transport positive holes such aspolymers having in the side chain thereof heterocyclic compoundstypified by poly-N-vinylcarbazole, triazole derivatives, oxadiazolederivatives, imidazole derivatives, pyrazoline derivatives,polyarylalcane derivatives, phenylenediamine derivatives, hydrazonederivatives, amino-substituted chalcone derivatives, triarylaminederivatives, carbazole derivatives, stilbene derivatives, phenothiazinederivatives, and the like.

The following are typical examples of the carrier-transport materialsuseful in this invention, but the carrier-transport materials usable inthis invention are not limited to the examples.

Formula [VIII] ##STR19## wherein R₁₆, R₁₇ and R₁₈ each is a hydrogenatom, an alkyl group, an alkoxy group, a halogen atom, a hydroxy group,a cyano group, a dialkylamino group, a diarylamino group, adiaralkylamino group, or a nitro group. Formula [IX] ##STR20## whereinR₁₉, R₂₂, R₂₃, R₂₄ and R₂₅ each is a hydrogen atom, an alkyl group, analkoxy group, a halogen atom, a hydroxy group, a cyano group, adialkylamino group, a diarylamino group, a diaralkylamino group or anitro group; R₂₀ is an alkyl group, a substitutable phenyl group, asubstitutable benzyl group, or a substitutable naphthyl group; and R₂₁is a hydrogen atom, an alkyl group, a cyano group or a substitutablephenyl group. Formula [X] ##STR21## wherein R₂₆, R₂₇, R₂₈ and R₂₉ eachis a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, ahydroxy group, a cyano group, a dialkylamino group, a diarylamino group,a diaralkylamino group or a nitro group; R is a hydrogen atom, asubstitutable phenyl group, a cyano group or an alkyl group; Ar is##STR22## wherein R₃₁, R₃₂ and R₃₃ each is an alkyl group, asubstitutable benzyl group, a substitutable phenyl group or asubstitutable naphthyl group; and R₃₄ is a hydrogen atom, an alkylgroup, an alkoxy group, a halogen atom, a hydroxy group, a cyano group,a dialkylamino group, a diarylamino group, diaralkylamino group, or anitro group. Formula [XI] ##STR23## wherein R₃₅, R₃₆, R₃₇ and R₃₈ eachis a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, ahydroxy group, a cyano group, a dialkylamino group, a diarylamino group,a diaralkylamino group, or a nitro group; R₃₉ is a hydrogen atom, asubstitutable phenyl group, a cyano group, or an alkyl group; Ar is##STR24## wherein R₄₀, R₄₁ and R₄₂ each is an alkyl group, asubstitutable benzyl group, a substitutable phenyl group, or asubstitutable naphthyl group; and R₄₃ is a hydrogen atom, an alkylgroup, an alkoxy group, a halogen atom, a hydroxy group, a cyano group,a dialkylamino group, a diarylamino group, a diaralkylamino group, or anitro group. Formula [XII] ##STR25## wherein R₄₄, R₄₅ and R₄₆ each is ahydrogen atom, an alkyl group, an alkoxy group, a halogen atom, ahydroxy group, a cyano group, a dialkylamino group, a diarylamino group,a diaralkylamino group, or a nitro group; and n is an integer of zeroor 1. Formula [XIII] ##STR26## wherein R₄₇, R₄₈, R₄₉, R₅₀, R₅₁ and R₅₂each is a hydrogen atom, an alkyl group, an alkoxy group, a halogenatom, a hydroxy group, a cyano group, a dialkylamino group, adiarylamino group, a diaralkylamino group, or a nitro group; and R₇ is ahydrogen atom or a phenyl group. Formula [XIV] ##STR27## wherein R₅₄,R₅₅, R₅₆, R₅₇, R₅₈ and R₅₉ each is a hydrogen atom, an alkyl group, analkoxy group, a halogen atom, a hydroxy group, a cyano group, adialkylamino group, a diarylamino group, a diaralkylamino group, or anitro group; and R₆₀ is a hydrogen atom or a phenyl group. Formula [XV]##STR28## wherein R₆₁, R₆₂, R₆₃, R₆₄, R₆₅ and R₆₆ each is a hydrogenatom, an alkyl group, an alkoxy group, a halogen atom, a hydroxy group,a cyano group, dialkylamino group, diarylamino group, a diaralkylaminogroup, or a nitro group.

The following are particular examples of the above-describedcarrier-transport materials:

Those having Formula [VIII]

    ______________________________________                                         ##STR29##                                                                    No.  R.sub.16       R.sub.17   R.sub.18                                       ______________________________________                                        T-1  H              H          H                                              T-2  CH.sub.3       H          H                                              T-3  CH.sub.3       CH.sub.3   H                                              T-4  CH.sub.3       C.sub.2 H.sub.5                                                                          H                                              T-5  CH.sub.3       OCH.sub.3  H                                              T-6  CH.sub.3       OC.sub.2 H.sub.5                                                                         H                                              T-7  CH.sub.3                                                                                      ##STR30## H                                              T-8  CH.sub.3                                                                                      ##STR31## H                                              T-9  CH.sub.3       Cl         H                                              T-10 CH.sub.3       NO.sub.2   H                                              T-11 CH.sub.3       CH.sub.3   CH.sub.3                                       T-12 CH.sub.3       CH.sub.3   OCH.sub.3                                      T-13 CH.sub.3       CH.sub.3   NO.sub.2                                       T-14 CH.sub.3       CH.sub.3                                                                                  ##STR32##                                     T-15 CH.sub.3       C.sub.2 H.sub.5                                                                          OCH.sub.3                                      T-16 CH.sub.3                                                                                      ##STR33##                                                                                ##STR34##                                     T-17 C.sub.2 H.sub.5                                                                              OC.sub.2 H.sub.5                                                                         OC.sub.2 H.sub.5                               T-18 C.sub.2 H.sub.5                                                                              H          H                                              T-19 OCH.sub.3      H          H                                              T-20 OC.sub.2 H.sub.5                                                                             H          H                                              T-21 Cl             H          H                                              T-22 I              H          H                                              T-23 Br             H          H                                              T-24 F              H          H                                              T-25 NO.sub.2       H          H                                              T-26                                                                                ##STR35##     H          H                                              T-27                                                                                ##STR36##     H          H                                              T-28                                                                                ##STR37##     H          H                                              T-29 CN             H          H                                              T-30 OH             H          H                                              T-31                                                                                ##STR38##     H          H                                              T-32 OCH.sub.3      OCH.sub.3  H                                              T-33 OCH.sub.3       OCH.sub.3 OCH.sub.3                                      T-34 NO.sub.2       NO.sub.2   NO.sub.2                                       T-35                                                                                ##STR39##                                                                                    ##STR40##                                                                                ##STR41##                                     T-36                                                                                ##STR42##     CH.sub.3   CH.sub.3                                       T-37                                                                                ##STR43##     Cl         H                                              T-38                                                                                ##STR44##                                                                                    ##STR45## OCH.sub.3                                      T-39                                                                                ##STR46##     H          H                                              T-40                                                                                ##STR47##     C.sub.2 H.sub.5                                                                          CH.sub.3                                       T-41                                                                                ##STR48##     OCH.sub.3  H                                              T-42 Br             Br         Br                                             ______________________________________                                    

Those having Formula [IX]

    __________________________________________________________________________     ##STR49##                                                                    No.                                                                              R.sub.19                                                                             R.sub.20  R.sub.21                                                                             R.sub.22                                                                           R.sub.23                                                                           R.sub.24     R.sub.25                    __________________________________________________________________________    T-43                                                                             H                                                                                     ##STR50##                                                                              H      H    H    H            H                           T-44                                                                             H                                                                                     ##STR51##                                                                              H      H    H    H            H                           T-45                                                                             H      C.sub.2 H.sub.5                                                                         H      H    H    H            H                           T-46                                                                             H      CH.sub.3  H      H    H    H            H                           T-47                                                                             H      CH.sub.3  H      H    H    CH.sub.3     H                           T-48                                                                             H      CH.sub.3  H      H    H    C.sub.2 H.sub.5                                                                            H                           T-49                                                                             H      CH.sub.3  H      H    H    OCH.sub.3    H                           T-50                                                                             H      CH.sub.3  H      H    H    OC.sub.2 H.sub.5                                                                           H                           T-51                                                                             H      CH.sub.3  H      H    H                                                                                   ##STR52##   H                           T-52                                                                             H      CH.sub.3  H      H    H                                                                                   ##STR53##   H                           T-53                                                                             H      CH.sub.3  H      H    H                                                                                   ##STR54##   H                           T-54                                                                             H      CH.sub.3  H      CH.sub.3                                                                           H    CH.sub.3     H                           T-55                                                                             H      CH.sub.3  H      Cl   H    CH.sub.3     H                           T-56                                                                             H      CH.sub.3  H      H    CH.sub.3                                                                           CH.sub.3     H                           T-57                                                                             H      CH.sub.3  H      H    CH.sub.3                                                                           H            CH.sub.3                    T-58                                                                             H      CH.sub.3  H      H    OCH.sub.3                                                                          OCH.sub.3    OCH.sub.3                   T-59                                                                             H      CH.sub.3  H      H    OCH.sub.3                                                                          OCH.sub.3    H                           T-60                                                                             H      CH.sub.3  H      OCH.sub.3                                                                          H    OCH.sub.3    H                           T-61                                                                             H      CH.sub.3  H      H    NO.sub.2                                                                           H            H                           T-62                                                                             H      CH.sub.3  H      H    H    OH           H                           T-63                                                                             H                                                                                     ##STR55##                                                                              H      H    H    H            H                           T-64                                                                             CH.sub.3                                                                             CH.sub.3  H      H    H                                                                                   ##STR56##   H                           T-65                                                                             C.sub.2 H.sub.5                                                                      CH.sub.3  H      H    H                                                                                   ##STR57##   H                           T-66                                                                             OCH.sub.3                                                                            CH.sub.3  H      CH.sub.3                                                                           H    CH.sub.3     H                           T-67                                                                             OC.sub.2 H.sub.5                                                                     CH.sub.3  H      Cl   H    CH.sub.3     H                           T-68                                                                             Cl     CH.sub.3  H      H    CH.sub.3                                                                           CH           H                           T-69                                                                              ##STR58##                                                                           CH.sub.3  H      H    CH.sub.3                                                                           H            CH.sub.3                    T-70                                                                              ##STR59##                                                                           CH.sub.3  H      H    OCH.sub.3                                                                          OCH.sub.3    OCH.sub.3                   T-71                                                                             NO.sub.2                                                                             CH.sub.3  H      H    OCH.sub.3                                                                          OCH.sub.3    H                           T-72                                                                             OH     CH.sub.3  H      OCH  H    OCH.sub.3    H                           T-73                                                                             CH.sub.3                                                                             CH.sub.3                                                                                 ##STR60##                                                                           H    NO.sub.2                                                                           H            H                           T-74                                                                             C.sub.2 H.sub.5                                                                      CH.sub.3  CN     H    H    OH           H                           T-75                                                                             OCH.sub.3                                                                            CH.sub.3  CH.sub.3                                                                             H    H    H            H                           T-76                                                                             H                                                                                     ##STR61##                                                                              H      H    H                                                                                   ##STR62##   H                           T-77                                                                             H                                                                                     ##STR63##                                                                              H      H    H                                                                                   ##STR64##   H                           T-78                                                                             H                                                                                     ##STR65##                                                                              H      CH.sub.3                                                                           H    CH.sub.3     H                           T-79                                                                             H                                                                                     ##STR66##                                                                              H      Cl   H    CH.sub.3     H                           T-80                                                                             CH                                                                                    ##STR67##                                                                              H      H    CH.sub.3                                                                           CH.sub.3     H                           T-81                                                                             OCH                                                                                   ##STR68##                                                                              H      H    CH.sub.3                                                                           H            CH.sub.3                    T-82                                                                             Cl                                                                                    ##STR69##                                                                              H      H    OCH.sub.3                                                                          OCH.sub.3    OCH.sub.3                   T-83                                                                              ##STR70##                                                                            ##STR71##                                                                              H      H    OCH.sub.3                                                                          OCH.sub. 3   H                           T-84                                                                             NO.sub.2                                                                              ##STR72##                                                                               ##STR73##                                                                           OCH.sub.3                                                                          H    OCH.sub.3    H                           T-85                                                                             CH.sub.3                                                                              ##STR74##                                                                              CN     H    NO.sub.2                                                                           H            H                           T-86                                                                             OC.sub.2 H.sub.5                                                                      ##STR75##                                                                              CH     H    H    OH           H                           T-87                                                                             Br                                                                                    ##STR76##                                                                              C.sub.2 H.sub.5                                                                      H    H    H            H                           T-88                                                                             H                                                                                     ##STR77##                                                                              H      H    H                                                                                   ##STR78##   H                           T-89                                                                             H                                                                                     ##STR79##                                                                              H      H    H                                                                                   ##STR80##   H                           T-90                                                                             H                                                                                     ##STR81##                                                                              H      CH.sub.3                                                                           H    CH.sub.3     H                           T-91                                                                             H                                                                                     ##STR82##                                                                               ##STR83##                                                                           Cl   H    CH.sub.3     H                           T-92                                                                             CH                                                                                    ##STR84##                                                                              CN     H    CH.sub.3                                                                           CH.sub.3     H                           T-93                                                                             OCH.sub.3                                                                             ##STR85##                                                                              H      H    CH.sub.3                                                                           H            CH.sub.3                    T-94                                                                             Cl                                                                                    ##STR86##                                                                              CH.sub.3                                                                             H    OCH.sub.3                                                                          OCH.sub.3    OCH.sub.3                   T-95                                                                              ##STR87##                                                                            ##STR88##                                                                              C.sub.2 H.sub.5                                                                      H    OCH.sub.3                                                                          OCH.sub.3    H                           T-96                                                                             NO.sub.2                                                                              ##STR89##                                                                              H      OCH.sub.3                                                                          H    OCH.sub.3    H                           T-97                                                                             CH.sub.3                                                                             C.sub.2 H.sub.5                                                                         H      H    NO.sub.2                                                                           H            H                           T-98                                                                             OC.sub.2 H.sub.5                                                                     C.sub.3 H.sub.7                                                                         H      H    H    OH           H                           T-99                                                                             Br     C.sub.4 H.sub.9                                                                         H      H    H    H            H                           __________________________________________________________________________

Those having Formula [X]

    __________________________________________________________________________     ##STR90##                                                                    No.  R.sub.26   R.sub.27                                                                           R.sub.28                                                                           R.sub.29                                                                          R.sub.30   Ar                                   __________________________________________________________________________    T-100                                                                              H          H    H    H   H                                                                                         ##STR91##                           T-101                                                                              H          H    H    H   H                                                                                         ##STR92##                           T-102                                                                              H          H    H    H   H                                                                                         ##STR93##                           T-103                                                                              H          H    H    H   H                                                                                         ##STR94##                           T-104                                                                              H          H    H    H   H                                                                                         ##STR95##                           T-105                                                                              H          H    H    H   H                                                                                         ##STR96##                           T-106                                                                              H          H    H    H   H                                                                                         ##STR97##                           T-107                                                                              H          H    H    H   H                                                                                         ##STR98##                           T-108                                                                              H          H    H    H   H                                                                                         ##STR99##                           T-109                                                                              H          H    H    H   H                                                                                         ##STR100##                          T-110                                                                              H          H    H    H   H                                                                                         ##STR101##                          T-111                                                                              H          H    H    H   H                                                                                         ##STR102##                          T-112                                                                              H          H    H    H   H                                                                                         ##STR103##                          T-113                                                                              H          H    H    H   H                                                                                         ##STR104##                          T-114                                                                              H          H    H    H   H                                                                                         ##STR105##                          T-115                                                                              H          H    H    H   H                                                                                         ##STR106##                          T-116                                                                              H          OCH.sub.3                                                                          H    H   H                                                                                         ##STR107##                          T-117                                                                              H          OCH.sub.3                                                                          H    H   H                                                                                         ##STR108##                          T-118                                                                              H          OCH.sub.3                                                                          H    H   H                                                                                         ##STR109##                          T-119                                                                              H          CH.sub.3                                                                           H    H   H                                                                                         ##STR110##                          T-120                                                                              H          CH.sub.3                                                                           H    H   H                                                                                         ##STR111##                          T-121                                                                              CH.sub.3   H    H    H   CH.sub.3                                                                                  ##STR112##                          T-122                                                                              H          CH   H    H   CH.sub.3                                                                                  ##STR113##                          T-123                                                                              H          H    CH   H   CN                                                                                        ##STR114##                          T-124                                                                              H          H    H    CH.sub.3                                                                          CN                                                                                        ##STR115##                          T-125                                                                               ##STR116##                                                                              H    H    H                                                                                  ##STR117##                                                                               ##STR118##                          T-126                                                                              H          OCH.sub.3                                                                          H    H                                                                                  ##STR119##                                                                               ##STR120##                          T-127                                                                              H          H    NO.sub.2                                                                           H                                                                                  ##STR121##                                                                               ##STR122##                          T-128                                                                              H          H    H    OH                                                                                 ##STR123##                                                                               ##STR124##                          T-129                                                                              H          H    H    H                                                                                  ##STR125##                                                                               ##STR126##                          T-130                                                                              H          H    H    H                                                                                  ##STR127##                                                                               ##STR128##                          T-131                                                                              H          H    H    H                                                                                  ##STR129##                                                                               ##STR130##                          T-132                                                                              H          H    H    H                                                                                  ##STR131##                                                                               ##STR132##                          __________________________________________________________________________

Those having Formula [XI]

    __________________________________________________________________________     ##STR133##                                                                   No.  R.sub.35   R.sub.36                                                                            R.sub.37                                                                          R.sub.38                                                                           R.sub.39  Ar                                   __________________________________________________________________________    T-133                                                                              H          H     H   H    H                                                                                        ##STR134##                          T-134                                                                              H          H     H   H    H                                                                                        ##STR135##                          T-135                                                                              H          H     H   H    H                                                                                        ##STR136##                          T-136                                                                              H          H     H   H    H                                                                                        ##STR137##                          T-137                                                                              H          H     H   H    H                                                                                        ##STR138##                          T-138                                                                              H          H     H   H    H                                                                                        ##STR139##                          T-139                                                                              H          H     H   H    H                                                                                        ##STR140##                          T-140                                                                              H          H     H   H    H                                                                                        ##STR141##                          T-141                                                                              H          H     H   H    H                                                                                        ##STR142##                          T-142                                                                              H          H     H   H    H                                                                                        ##STR143##                          T-143                                                                              H          H     H   H    H                                                                                        ##STR144##                          T-144                                                                              H          H     H   H    H                                                                                        ##STR145##                          T-145                                                                              H          H     H   H    H                                                                                        ##STR146##                          T-146                                                                              H          H     H   H    H                                                                                        ##STR147##                          T-147                                                                              H          H     H   H    H                                                                                        ##STR148##                          T-148                                                                              H          H     H   H    H                                                                                        ##STR149##                          T-149                                                                              H          OCH.sub.3                                                                           H   H    H                                                                                        ##STR150##                          T-150                                                                              H          OCH.sub.3                                                                           H   H    H                                                                                        ##STR151##                          T-151                                                                              H          OCH.sub.3                                                                           H   H    H                                                                                        ##STR152##                          T-152                                                                              H          CH.sub.3                                                                            H   H    H                                                                                        ##STR153##                          T-153                                                                              H          CH.sub.3                                                                            H   H    H                                                                                        ##STR154##                          T-154                                                                              CH.sub.3   H     H   H    CH.sub.3                                                                                 ##STR155##                          T-155                                                                              H          CH.sub.3                                                                            H   H    CH.sub.3                                                                                 ##STR156##                          T-156                                                                              H          H     CH  H    CN                                                                                       ##STR157##                          T-157                                                                              H          H     H   CH.sub.3                                                                           CN                                                                                       ##STR158##                          T-158                                                                               ##STR159##                                                                              H     H   H                                                                                   ##STR160##                                                                              ##STR161##                          T-159                                                                              H          OCH.sub.3                                                                           H   H                                                                                   ##STR162##                                                                              ##STR163##                          T-160                                                                              H          H     NO.sub.2                                                                          H                                                                                   ##STR164##                                                                              ##STR165##                          T-161                                                                              H          H     H   OH                                                                                  ##STR166##                                                                              ##STR167##                          T-162                                                                              H          H     H   H                                                                                   ##STR168##                                                                              ##STR169##                          T-163                                                                              H          H     H   H                                                                                   ##STR170##                                                                              ##STR171##                          T-164                                                                              H          H     H   H                                                                                   ##STR172##                                                                              ##STR173##                          T-165                                                                              H          H     H   H                                                                                   ##STR174##                                                                              ##STR175##                          __________________________________________________________________________

Those having Formula [XIII]

    __________________________________________________________________________     ##STR176##                                                                   No. R.sub.44                                                                              R.sub.45      R.sub.46      n                                     __________________________________________________________________________    T-166                                                                             H       H             H             0                                     T-167                                                                             H       H             CH.sub.3      1                                     T-168                                                                             H       H             C.sub.2 H.sub.5                                                                             0                                     T-169                                                                             H       H             OCH.sub.3     1                                     T-170                                                                             H       H             OC.sub.2 H.sub.5                                                                            0                                     T-171                                                                             H       H             Cl            1                                     T-172                                                                             H       H             Br            1                                     T-173                                                                             H       H             F             1                                     T-174                                                                             H       H             I             1                                     T-175                                                                             H       H                                                                                            ##STR177##   0                                     T-176                                                                             H       H                                                                                            ##STR178##   1                                     T-177                                                                             H       H                                                                                            ##STR179##   0                                     T-178                                                                             H       H                                                                                            ##STR180##   1                                     T-179                                                                             H       H             CN            0                                     T-180                                                                             H       H             NO.sub.2      1                                     T-181                                                                             H       H             OH            1                                     T-182                                                                             H       H             C.sub.8 H.sub.17                                                                            1                                     T-183                                                                             CH.sub.3                                                                              H             H             1                                     T-184                                                                             CH.sub.3                                                                              H             CH.sub.3      1                                     T-185                                                                             CH.sub.3                                                                              H             OCH.sub.3     1                                     T-186                                                                             CH.sub.3                                                                              H             Cl            1                                     T-187                                                                             CH.sub.3                                                                              H                                                                                            ##STR181##   1                                     T-188                                                                             OCH.sub.3                                                                             CH.sub.3                                                                                     ##STR182##   1                                     T-189                                                                             OCH.sub.3                                                                             OCH.sub.3     OCH.sub.3     1                                     T-190                                                                             OCH.sub.3                                                                              ##STR183##   H             1                                     T-191                                                                             Cl                                                                                     ##STR184##   H             1                                     T-192                                                                             OH      OH            OH            1                                     T-l93                                                                              ##STR185##                                                                           H             H             1                                     T-194                                                                              ##STR186##                                                                           H             OCH.sub.3     1                                     T-195                                                                              ##STR187##                                                                           H                                                                                            ##STR188##   1                                     T-196                                                                             H                                                                                      ##STR189##   CH.sub.3      1                                     T-197                                                                             H                                                                                      ##STR190##   OCH.sub.3     1                                     T-198                                                                             H       CN            H             1                                     __________________________________________________________________________

Those having Formula [XIII]

    __________________________________________________________________________     ##STR191##                                                                   No. R.sub.47                                                                           R.sub.48                                                                           R.sub.49                                                                           R.sub.50     R.sub.51                                                                           R.sub.52                                                                          R.sub.53                             __________________________________________________________________________    T-199                                                                             H    H    H    H            H    H   H                                    T-200                                                                             H    H    H    CH.sub.3     H    H   H                                    T-201                                                                             H    H    H    OCH.sub.3    H    H   H                                    T-202                                                                             H    H    H    Cl           H    H   H                                    T-203                                                                             H    H    Cl   H            H    H   H                                    T-204                                                                             H    H    CH.sub.3                                                                           H            H    H   H                                    T-205                                                                             H    H    OCH.sub.3                                                                          H            H    H                                                                                  ##STR192##                          T-206                                                                             H    H    H    H            H    H                                                                                  ##STR193##                          T-207                                                                             H    H    H    CH           H    H                                                                                  ##STR194##                          T-208                                                                             H    CH.sub.3                                                                           H    H            H    H   H                                    T-209                                                                             H    CH.sub.3                                                                           H    CH.sub.3     H    H   H                                    T-210                                                                             H    CH.sub.3                                                                           H    OCH.sub.3    H    H   H                                    T-211                                                                             H    CH.sub.3                                                                           H                                                                                   ##STR195##  H    H   H                                    T-212                                                                             H    CH.sub.3                                                                           CH   H            H    H   H                                    T-213                                                                             H    CH.sub.3                                                                           Cl   H            H    H   H                                    T-214                                                                             H    CH.sub.3                                                                           H    CH           CH.sub.3                                                                           H   H                                    T-215                                                                             H    CH.sub.3                                                                           OCH.sub.3                                                                          OCH.sub.3    OCH.sub.3                                                                          H   H                                    T-216                                                                             H    CH.sub.3                                                                           H    H            NO.sub.2                                                                           H   H                                    T-217                                                                             H    CH.sub.3                                                                           H    H            H    H                                                                                  ##STR196##                          T-218                                                                             H    CH.sub.3                                                                           H    CH.sub.3     H    H                                                                                  ##STR197##                          T-219                                                                             H    CH.sub.3                                                                           H    Br           H    H                                                                                  ##STR198##                          T-220                                                                             H    OCH.sub.3                                                                          H    H            H    H   H                                    T-221                                                                             H    OCH.sub.3                                                                          H    CH.sub.3     H    H   H                                    T-222                                                                             H    OCH.sub.3                                                                          H    OCH.sub.3    H    H   H                                    T-223                                                                             H    OCH.sub.3                                                                          H    Br           H    H   H                                    T-224                                                                             H    OCH.sub.3                                                                          OCH.sub.3                                                                          H            H    H   H                                    T-225                                                                             H    OCH.sub.3                                                                          NO.sub.2                                                                           H            H    H   H                                    T-226                                                                             H    OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3    H    H   H                                    T-227                                                                             H    OCH.sub.3                                                                          CH.sub.3                                                                           H            H    CH.sub.3                                                                          H                                    T-228                                                                             H    OCH.sub.3                                                                          H    C.sub.2 H.sub.5                                                                            H    H   H                                    T-229                                                                             H    OCH.sub.3                                                                          H    H            H    H                                                                                  ##STR199##                          T-230                                                                             H    OCH.sub.3                                                                          H    CH.sub.3     H    H                                                                                  ##STR200##                          T-231                                                                             H    OCH.sub.3                                                                          OCH.sub.3                                                                          H            H    H                                                                                  ##STR201##                          T-232                                                                             CH.sub.3                                                                           CH.sub.3                                                                           H    H            H    H   H                                    T-233                                                                             CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.3     H    H   H                                    T-234                                                                             CH.sub.3                                                                           CH.sub.3                                                                           H    OCH.sub.3    H    H   H                                    T-235                                                                             CH.sub.3                                                                           CH.sub.3                                                                           H    Cl           H    H   H                                    T-236                                                                             CH.sub.3                                                                           CH.sub.3                                                                           H    Br           H    H   H                                    T-237                                                                             CH.sub.3                                                                           CH.sub.3                                                                           CH   H            H    H   H                                    T-238                                                                             CH.sub.3                                                                           CH.sub.3                                                                           OCH  H            H    H   H                                    T-239                                                                             CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3    H    H   H                                    T-240                                                                             CH.sub.3                                                                           CH.sub.3                                                                           H    H            H    H                                                                                  ##STR202##                          T-241                                                                             CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                          OCH.sub.3    OCH.sub.3                                                                          H                                                                                  ##STR203##                          T-242                                                                             CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                          OCH.sub.3    H    H                                                                                  ##STR204##                          T-243                                                                             CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           H            H    H                                                                                  ##STR205##                          T-244                                                                             CH.sub.3                                                                           OCH.sub.3                                                                          H    H            H    H   H                                    T-245                                                                             CH.sub.3                                                                           OCH.sub.3                                                                          H    CH.sub.3     H    H   H                                    T-246                                                                             CH.sub.3                                                                           OCH.sub.3                                                                          H    OCH.sub.3    H    H   H                                    T-247                                                                             CH.sub.3                                                                           OCH.sub.3                                                                          H    Cl           H    H   H -T-248 CH.sub.3 OCH.sub.3 CH.su                                             b.3 H H H H                          T-249                                                                             CH.sub.3                                                                           OCH.sub.3                                                                          CH.sub.3                                                                           CH.sub.3     H    H   H                                    T-250                                                                             CH.sub.3                                                                            OCH.sub.3                                                                         OCH.sub.3                                                                          OH           OCH.sub.3                                                                          H   H                                    T-251                                                                             CH.sub.3                                                                           OCH.sub.3                                                                          H                                                                                   ##STR206##  H    H   H                                    T-252                                                                             CH.sub.3                                                                           OCH.sub.3                                                                          H    H            H    H                                                                                  ##STR207##                          T-253                                                                             CH.sub.3                                                                           OCH.sub.3                                                                          H                                                                                   ##STR208##  H    H                                                                                  ##STR209##                          T-254                                                                             CH.sub.3                                                                           OCH.sub.3                                                                          NO.sub.2                                                                           H            H    H                                                                                  ##STR210##                          T-255                                                                             CH.sub.3                                                                           OCH.sub.3                                                                          H    OCH.sub.3    H    H                                                                                  ##STR211##                          T-256                                                                             OCH.sub.3                                                                          OCH.sub.3                                                                          H    H            H    H   H                                    T-257                                                                             OCH.sub.3                                                                          OCH.sub.3                                                                          H    CH.sub.3     H    H   H                                    T-258                                                                             OCH.sub.3                                                                          OCH.sub.3                                                                          H    OCH.sub.3    H    H   H                                    T-259                                                                             OCH.sub.3                                                                          OCH.sub.3                                                                          H    F            H    H   H                                    T-260                                                                             OCH.sub.3                                                                          OCH.sub.3                                                                          H                                                                                   ##STR212##  H    H   H                                    T-261                                                                             OCH.sub.3                                                                          OCH.sub.3                                                                          H    CN           H    H   H                                    T-262                                                                             OCH.sub.3                                                                          OCH.sub.3                                                                          NO.sub.2                                                                           H            H    H   H                                    T-263                                                                             OCH.sub.3                                                                          OCH.sub.3                                                                          H    OH           H    H   H                                    T-264                                                                             OCH.sub.3                                                                          OCH.sub.3                                                                          H    H            H    H                                                                                  ##STR213##                          T-265                                                                             OCH.sub.3                                                                          OCH.sub.3                                                                          H    CH.sub.3     H    H                                                                                  ##STR214##                          T-266                                                                             OCH.sub.3                                                                          OCH.sub.3                                                                          H    OCH.sub.3    H    H                                                                                  ##STR215##                          T-267                                                                             OCH.sub.3                                                                          OCH.sub.3                                                                          H    H            H    Cl                                                                                 ##STR216##                          T-268                                                                             H    C.sub.2 H.sub.5                                                                    H    H            H    H   H                                    T-269                                                                             H    C.sub.2 H.sub.5                                                                    H    CH.sub.3     H    H                                                                                  ##STR217##                          T-270                                                                             C.sub.2 H.sub.5                                                                    C.sub.2 H.sub.5                                                                    H    OCH.sub.3    H    H   H                                    T-271                                                                             H    OCH  CH   H            H    H                                                                                  ##STR218##                          T-272                                                                             H    OC.sub.2 H.sub.5                                                                   Br   H            H    H   H                                    T-273                                                                             H                                                                                   ##STR219##                                                                        H    H            H    Cl  H                                    T-274                                                                             H                                                                                   ##STR220##                                                                        H    H            H    CH.sub.3                                                                           ##STR221##                          T-275                                                                             NO.sub.2                                                                           NO.sub.2                                                                           NO.sub.2                                                                           H            H    H                                                                                  ##STR222##                          T-276                                                                             H    NO.sub.2                                                                           CH.sub.3                                                                           CH.sub.3     H    H                                                                                  ##STR223##                          T-277                                                                             H    OH   H                                                                                   ##STR224##  H    H   H                                    T-278                                                                             OH   OH   CN   H            H    H   H                                    T-279                                                                             OH   CH.sub.3                                                                           H                                                                                   ##STR225##  H    H   H                                    __________________________________________________________________________

Those having Formula [XIV]

    __________________________________________________________________________     ##STR226##                                                                   No. R.sub.54                                                                             R.sub.55  R.sub.56                                                                           R.sub.57     R.sub.58                                                                           R.sub.59                                                                         R.sub.60                       __________________________________________________________________________    T-280                                                                             H      H         H    H            H    H  H                              T-281                                                                             H      H         H    CH.sub.3     H    H  H                              T-282                                                                             H      H         H    OCH.sub.3    H    H  H                              T-283                                                                             H      H         CH.sub.3                                                                           H            H    H  H                              T-284                                                                             H      H         OCH.sub.3                                                                          H            H    H  H                              T-285                                                                             H      H         H    Cl           H    H  H                              T-286                                                                             H      H         CH.sub.3                                                                           CH.sub.3     H    H                                                                                 ##STR227##                    T-287                                                                             H      H         OCH.sub.3                                                                          OCH.sub.3    H    H                                                                                 ##STR228##                    T-288                                                                             H      H         NO.sub.2                                                                           H            H    H                                                                                 ##STR229##                    T-289                                                                             H      CH.sub.3  H    H            H    H  H                              T-290                                                                             H      CH.sub.3  H    CH.sub.3     H    H  H                              T-291                                                                             H      CH.sub.3  H    OCH.sub.3    H    H  H                              T-292                                                                             H      CH.sub.3  CH   H            H    H  H                              T-293                                                                             H      CH.sub.3  OCH  H            H    H  H                              T-294                                                                             H      CH.sub.3  H    H            H    Cl H                              T-295                                                                             H      CH.sub.3  H    H            H    Br H                              T-296                                                                             H      CH.sub.3  NO.sub.2                                                                           H            H    H  H                              T-297                                                                             H      CH.sub.3  H                                                                                   ##STR230##  H    H                                                                                 ##STR231##                    T-298                                                                             H      CH.sub.3  H    H            H    H                                                                                 ##STR232##                    T-299                                                                             H      CH.sub.3  H    OCH.sub.3    H    H                                                                                 ##STR233##                    T-300                                                                             H      CH.sub.3  H    CN           H    H                                                                                 ##STR234##                    T-301                                                                             H      OCH.sub.3 H    H            H    H  H                              T-302                                                                             H      OCH.sub.3 H    CH.sub.3     H    H  H                              T-303                                                                             H      OCH.sub.3 H    OCH.sub.3    H    H  H                              T-304                                                                             H      OCH.sub.3 H                                                                                   ##STR235##  H    H  H                              T-305                                                                             H      OCH.sub.3 H                                                                                   ##STR236##  H    H  H                              T-306                                                                             H      OCH.sub.3 NO.sub.2                                                                           H            H    H  H                              T-307                                                                             H      OCH.sub.3 H    H            H    Cl H                              T-308                                                                             H      OCH.sub.3 H    H            H    Br H                              T-309                                                                             H      OCH.sub.3 H    H            H    H                                                                                 ##STR237##                    T-310                                                                             H      OCH.sub.3 CH.sub.3                                                                           CH.sub.3     H    H                                                                                 ##STR238##                    T-311                                                                             H      OCH.sub.3 OCH.sub.3                                                                          OCH.sub.3    OCH.sub.3                                                                          H                                                                                 ##STR239##                    T-312                                                                             H      OCH.sub.3 H    OH           H    H                                                                                 ##STR240##                    T-313                                                                             H      C.sub.2 H.sub.5                                                                         H    H            H    H  H                              T-314                                                                             H      C.sub.2 H.sub.5                                                                         H    CH           H    H  H                              T-315                                                                             H      OC.sub.2 H.sub.5                                                                        H    H            H    H  H                              T-316                                                                             H      OC.sub.2 H.sub.5                                                                        H    CH           H    H  H                              T-317                                                                             H                                                                                     ##STR241##                                                                             H    H            H    H  H                              T-318                                                                             H                                                                                     ##STR242##                                                                             H    H            H    H  H                              T-319                                                                             H      Cl        H    H            H    H  H                              T-320                                                                             H      Br        H    Br           H    H  H                              T-321                                                                             H      OH        H    OH           H    H                                                                                 ##STR243##                    T-322                                                                             H      CN        H    CH.sub.3     H    H                                                                                 ##STR244##                    T-323                                                                             H      NO.sub.2  H    OCH.sub.3    H    H                                                                                 ##STR245##                    T-324                                                                             H      C.sub.8 H.sub.17                                                                        H                                                                                   ##STR246##  H    H                                                                                 ##STR247##                    T-325                                                                             CH.sub.3                                                                             H         H    H            H    H  H                              T-326                                                                             CH.sub.3                                                                             CH.sub.3  H    CH.sub.3     H    H  H                              T-327                                                                             CH.sub.3                                                                              ##STR248##                                                                             H    H            H    H  H                              T-328                                                                             OCH.sub.3                                                                            H         H    CH.sub.3     H    H  H                              T-329                                                                             OCH.sub.3                                                                            OCH.sub.3 H    OCH.sub.3    H    H  H                              T-330                                                                             OCH.sub.3                                                                            Cl        H    Cl           H    H  H                              T-331                                                                             NO.sub.2                                                                             Br        H    H            H    H  H                              T-332                                                                             NO.sub.2                                                                             F         H    Br           H    H  H                              T-333                                                                             Cl                                                                                    ##STR249##                                                                             H    H            H    H                                                                                 ##STR250##                    T-334                                                                             Br     Br        H    CH.sub.3     H    H                                                                                 ##STR251##                    T-335                                                                             F      CN        H    OCH.sub.3    H    H                                                                                 ##STR252##                    T-336                                                                              ##STR253##                                                                          OH        H    H            H    H                                                                                 ##STR254##                    __________________________________________________________________________

Those having Formula [XV]

    ______________________________________                                         ##STR255##                                                                   No.   R.sub.61  R.sub.62                                                                              R.sub.63                                                                            R.sub.64                                                                            R.sub.65                                                                             R.sub.66                           ______________________________________                                        T-337 H         H       H     H     H      H                                  T-338 NO.sub.2  H       H     H     H      H                                  T-339 Cl        H       H     H     H      H                                  T-340 H         H       H     H     H      CH.sub.3                           T-341 Cl        H       H     Cl    H      CH.sub.3                           T-342 H         Cl      Cl    H     H      CH.sub.3                           T-343 H         H       H     H     H      OCH.sub.3                          T-344 OCH.sub.3 H       H     H     H      OCH.sub.3                          T-345 CH.sub.3  H       H     H     H      OCH.sub.3                          T-346 H         H       H     H     CH.sub.3                                                                             CH.sub.3                           T-347 Cl        H       H     H     CH.sub.3                                                                             CH.sub.3                           T-348 OCH.sub.3 H       H     H     CH.sub.3                                                                             CH.sub.3                           T-349 H         H       H     H     CH.sub.3                                                                             OCH.sub. 3                         T-350 Cl        H       H     H     CH.sub.3                                                                             OCH.sub.3                          T-351 OCH.sub.3 H       H     H     CH.sub.3                                                                             OCH.sub.3                          T-352 H         H       H     H     OCH.sub.3                                                                            OCH.sub.3                          T-353 Cl        H       H     H     OCH.sub.3                                                                            OCH.sub.3                          T-354 OCH.sub.3 H       H     H     OCH.sub.3                                                                            OCH.sub.3                          T-355 H         H       H     H     C.sub.8 H.sub.17                                                                     C.sub.8 H.sub.17                   T-356 H         H       H     H     Cl     Cl                                 T-357 H         H       H     H     CN     CN                                 ______________________________________                                    

The carrier-generating layer may be formed by either of the followingmethods:

(M-1) A method in which a solution prepared by dissolving an azocompound into an appropriate solvent and, if necessary, additionallymixing a binder thereinto is coated.

(M-2) A method in which a dispersion liquid prepared by making an azocompound finely particulate in a dispersion medium by means of a ballmill or homomixer and, if necessary, additionally mixing a binderthereinto is coated.

The solvent or dispersion medium for use in the formation of thecarrier-generating layer include n-butylamine, diethylamine, ethylenediamine, isopropanolamine, triethanolamine, triethylenediamine,N,N-dimethylformamide, acetone, methylethyl ketone, cyclohexanone,benzene, toluene, xylene, chloroform, 1,2-dichloroethane,dichloromethane, tetrahydrofuran, dioxane, methanol, ethanol,isopropanol, ethyl acetate, butyl acetate, dimethyl sulfoxide, and thelike.

The binder to be used for the carrier-generating layer orcarrier-transport layer may be any discretional one, but is desirable tobe an electric-insulating film-formable high-molecular polymer which ishydrophobic and highly dielectric. Such high-molecular polymers include,e.g., the following examples, but are not limited thereto:

(P-1) Polycarbonate

(P-2) Polyester

(P-3) Methacrylic resin

(P-4) Acrylic resin

(P-5) Polyvinyl chloride

(P-6) Polyvinylidene chloride

(P-7) Polystyrene

(P-8) Polyvinyl acetate

(P-9) Styrene-butadiene copolymer

(P-10) Vinylidene chloride-acrylonitrile copolymer

(P-11) Vinyl chloride-vinyl acetate copolymer

(P-12) Vinyl chloride-vinyl acetate-maleic anhydride copolymer

(P-13) Silicone resin

(P-14) Silicone-alkyd resin

(P-15) Phenol-formaldehyde resin

(P-16) Styrene-alkyd resin

(P-17) Poly-N-vinylcarbazole

(P-18) Polyvinyl butyral

(P-19) Polyvinyl formal

These binder materials may be used along or in a mixture of two or moreof them.

The thickness of the thus formed carrier-generating layer 2 ispreferably from 0.01 μm to 20 μm, and more preferably from 0.05 μm to 5μm. The particle size of the azo compound in the case where thecarrier-generating layer or photosensitive layer is of the dispersiontype is preferably not more than 5 μm, and more preferably not more than1 μm.

The conductive support material applicable to the photoreceptor of thisinvention includes metallic plates or drums whose metals include alloys:conductive polymers; paper made conductive by being coated,vacuum-deposited or laminated thereon with a conductive compound such asindium oxide or with a metallic thin layer such as of aluminum,palladium, gold, etc., or an alloy therof; and the like. Those usable asthe interlayer such as an adhesion layer or barrier layer includeorganic high-molecular materials such as polyvinyl alcohol, ethylcellulose, carboxymethyl cellulose, and inorganic materials such asaluminum oxide, etc., in addition to the foregoing high-molecularpolymers used as the binder.

The photoreceptor of this invention is as has been described above. Aswill be apparent from the following examples the photoreceptor isexcellent in the chargeability, sensitivity and image formability, andso excellently durable that it is hardly fatigued or deteriorated evenwhen repeatedly used.

The present invention will be illustrated in detail by the followingexamples, but the embodiments of the invention are not limited by theexamples.

EXAMPLES Example 1

Two grams of Exemplified Compound A-1 and 2 g of polycarbonate resin"Panlite L-1250" (manufactured by Teijin Chemical Industry Co., Ltd.)were added to 110 ml of 1,2-dichloroethane, and were dispersed over aperiod of 12 hours by means of a ball mill. This dispersed liquid wascoated on an aluminum-vacuum-deposited polyester film so that the drythickness is 0.3 μm to thereby form a carrier-generating layer, andfurther on this was coated a liquid as a carrier-transport layerprepared by dissolving 6 g of the foregoing compound T-201 and 10 g ofpolycarbonate resin "Panlite L-1250" into 110 ml of 1,2-dichloroethaneso that the dry thickness is 15 μm, whereby a photoreceptor of thisinvention was prepared.

The thus obtained photoreceptor was evaluated with respect to thefollowing characteristics by use of an electronic paper tester ModelSP-428, manufactured by Kawaguchi Denki Seisakusho K.K. Thephotoreceptor was charged for five seconds at a charging voltage of -6KV, then allowed to stand for five seconds in the dark, and then exposedto a halogen lamp light so that the illuminance on the photosensitivesurface of the photoreceptor is 35 luxes to thereby find the exposure(half-exposure) E 2/1 that is required for reducing the surfacepotential by half. Also, the surface potential (residual potential)V_(R) of the photoreceptor after being subjected to a 30-lux.secexposure was found. Further, the same tests and measurements wererepeated 100 times. The obtained results are as given in Table 1.

                  TABLE 1                                                         ______________________________________                                                        First                                                                              100th                                                    ______________________________________                                        E 1/2 (lux.sec)   2.4    2.5                                                  V.sub.R           0      0                                                    ______________________________________                                    

Comparative Example 1

A comparative photoreceptor was prepared in the same manner as inExample 1 except that the following bisazo compound C-(1) was used asthe carrier-generating material.

C-(1) ##STR256##

This comparative photoreceptor was measured in the same manner as inExample 1, and the results as shown in Table 2 were obtained.

                  TABLE 2                                                         ______________________________________                                                       First                                                                              100th                                                     ______________________________________                                        E 1/2 (lux.sec)  6.0    6.9                                                   V.sub.R (V)      0      -10                                                   ______________________________________                                    

As is apparent from the above table, the photoreceptor of this inventionis very excellent in the sensitivity as well as in the residualpotential, and also in the stability when used repeatedly, as comparedto the comparative photoreceptor.

Examples 2 through 4

Photoreceptor samples of this invention were prepared in the same manneras in Example 1 except that Exemplified Compounds A-4, A-32 and A-50were used as the carrier-generating material, and the foregoingcompounds T-174, T-188 and T-185 were used as the carrier-transportmaterial. These resulting photoreceptors were tested and measured in thesame manner as in Example 1, whereby the results as given in Table 3were obtained.

                                      TABLE 3                                     __________________________________________________________________________    Example          First      100th                                             No.  Azo compound                                                                              E 1/2 (lux.sec)                                                                      V.sub.R (V)                                                                       E 1/2 (lux.sec)                                                                      V.sub.R (V)                                __________________________________________________________________________    1    Exemplified Compound                                                                      1.9    0   1.8    0                                               A-4                                                                      2    Exemplified Compound                                                                      2.6    0   2.7    0                                               A-32                                                                     3    Exemplified Compound                                                                      3.0    0   3.2    0                                               A-50                                                                     __________________________________________________________________________

Example 5

On an aluminum foil-laminated polyester film conductive support wasprovided on 0.05 μm-thick interlayer comprised of a vinyl chloride-vinylacetate-maleic anhydride copolymer "Eslec MF-10" (a product of SekisuiChemical Co., Ltd.), and on this was coated a dispersion liquid preparedby mixing and dispersing 2 g of Exemplified Compound A-5 into 110 ml of1,2-dichloroethane for 24 hours by means of a ball mill to thereby forma carrier-generating layer so that the dry thickness is 0.5 μm. On thiscarrier-generating layer was coated a solution of 6 g of the foregoingcompound T-109 and 10 g of a methacrylic resin "Acrypet" (a product ofMitsubishi Rayon Co., Ltd.) both dissolved in 70 ml of1,2-dichloroethane to thereby form a carrier-transport layer so that thedry thickness is 10 μm, whereby a photoreceptor of this invention wasobtained.

This photoreceptor sample was tested and measured in the same manner asin Example 1, whereby the first test results E 1/2=2.2 lux.sec and V_(R)=0_(V) were obtained.

Example 6

On the same interlayer-provided conductive support as that used inExample 5 was coated an ethylenediamine 1% Exemplified Compound A-98solution so that the dry thickness is 0.1 μm, whereby acarrier-generating layer was formed. After that, on this was coated asolution of 6 g of the foregoing compound T-213 and 10 g of a polyesterresin "Vylon 200" (a product of Toyo Spinning Co., Ltd.) both dissolvedin 70 ml of 1,2-dichloroethane to thereby form a carrier-transport layerso that the dry thickness is 12 μm, whereby a photoreceptor of thisinvention was prepared.

This photoreceptor sample was tested and measured in the same manner asin Example 1, whereby the results as given in Table 4 were obtained.

Comparative Example 2

A photoreceptor sample was prepared in the same manner as in Example 6except that the Exemplified Compound A-98 used in Example 6 was replacedby bisazo compound C-(2) having the following structural formula.

The thus obtained photoreceptor was tested and measured in the samemanner as in Example 1, and the results obtained are shown in Table 4.

C-(2) ##STR257##

                  TABLE 4                                                         ______________________________________                                                First        100th                                                            E 1/2 (lux.sec)                                                                        V.sub.R (V)                                                                           E 1/2 (lux.sec)                                                                          V.sub.R (V)                               ______________________________________                                        Example 6 2.9        0       3.0      0                                       Comparative                                                                             6.5        0       10.4     -30                                     example 2                                                                     ______________________________________                                    

Example 7

A carrier-generating layer was formed in the same manner as in Example 5except that the Exemplified Compound A-5 was replaced by ExemplifiedCompund A-21. On this was coated a solution of 6 g of the foregoingcompound T-212 and 10 g of a polycarbonate "Panlite L-1250" (a productof Teijin Chemical Industry Co., Ltd.) both dissolved in 70 ml of1,2-dichloroethane to thereby form a carrier-transport layer so that thedry thickness is 20 μm, whereby a photoreceptor of this invention wasprepared.

This photoreceptor sample was tested and measured in the same manner asin Example 1, and the results were E 1/2=2.3 lux.sec and V_(R) =0_(V).

Example 8

On the surface of a 100 mm-diameter aluminum drum was provided a 0.05μm-thick interlayer comprises of a vinyl chloride-vinyl acetate-maleicanhydride copolymer "Eslec MF-10" (a product of Sekisui Chemical Co.,Ltd.), and on this was coated a dispersion liquid of 4 g of ExemplifiedCompound A-3 mixed and dispersed for 24 hours by a ball mill into 400 mlof 1,2-dichloroethane to thereby form a carrier-generating layer so thatthe dry thickness is 0.6 μm.

Further on this was coated a solution of 30 g of the foregoing compoundT-112 and 50 g of a polycarbonate resin "Iupilon S-1000" (a product ofMitsubishi Gas Chemicals Co., Ltd.) both dissolved in 400 ml of1,2-dichloroethane to form a carrier-transport layer so that the drythickness is 25 μm, whereby a drum-form electrophotographicphotoreceptor was prepared.

The thus prepared photoreceptor drum was loaded in a remodelled unit ofElectrophotographic Copier U-Bix 1600MR (manufactured by KonishirokuPhoto Industry Co., Ltd.) to make copies of an image, and as a result,very-true-to-the-original and clear image copies were obtained. Thequality of the reproduced image was unchanged even after repeating thecopying operation 10,000 times.

Comparative Example 3

A drum-form comparative photoreceptor was prepared in the same manner asin Example 8 except that the Exemplified Compound A-3 used in Example 8was replaced by bisazo compound C-(3) having the following structuralformula, and then evaluated with respect to the quality of the imagecopies obtained therefrom in the same manner as in Example 8, and as aresult, none but fogged image copies were obtained. And as the copyingis repeated, the contrast of the copy image becomes lowered, and almostno appreciable copy image was obtained after 2000-time copyingoperations.

C-(3) ##STR258## Example 9

On an aluminum foil-laminated polyester film conductive support wasprovided a 0.05 μm-thick interlayer comprised of a vinyl chloride-vinylacetate-maleic anhydride copolymer "Eslec MF-10" (a product of SekisuiChemical Co., Ltd.), and then on this was coated a dispersion liquid of5 g of Exemplified Compound A-16 and 3.3 g of a polycarbonate resin"Panlite L-1250" (a product of Teijin Chemical Industry Co., Ltd.) addedto and dispersed for 24 hours by means of a ball mill into 100 ml ofdichloromethane to form a layer so that the dry thickness is 10 μm,whereby a photoreceptor was prepared.

The thus obtained photoreceptor sample was tested and measured in thesame manner as in Example 1 with respect to E 1/2 and V_(R), and thefirst result were E 1/2=4.1 lux.sec and V_(R) =+3v

Example 10

On an aluminum-deposited polyester film was provided a carrier-transportlayer by coating a solution of 6 g of the foregoing compound T-119 and10 g of a polyester resin "Vylon 200" (a product of Toyo Spinning Co.,Ltd.) dissolved in 70 ml of 1,2-dichloroethane so that the dry thicknessis 10 μm.

On this was then coated a dispersion liquid of 1 g of ExemplifiedCompound A-202 and 1 g of Exemplified Compound A-1 both mixed anddispersed for 24 hours by means of a ball mill into 110 ml of1,2-dichloroethane to form a carrier-generating layer so that the drythickness is 0.5 μm, whereby a photoreceptor of this invention wasprepared.

The thus obtained photoreceptor was evaluated in the same manner as inExample 9, and the results were E 1/2=1.9 lux.sec and V_(R) =+5v.

Example 11

On an aluminum foil-laminated polyester film conductive support wasprovided a 0.05 μm-thick interlayer comprised of a vinyl chloride-vinylacetate-maleic anhydride copolymer "Eslec MF-10" (a product of SekisuiChemical Co., Ltd.), and on this was then coated a dispersion liquid of4 g of Exemplified Compound A-101, 8 g of the foregoing compound T-210,and 3 g of a polycarbonate resin "Panlite L-1250" (a product of TeijinChemical Industry Co., Ltd.) all added to and dispersed for 24 hours bymeans of a sand grinder into 100 ml of dichloroethane to form a layer sothat the dry thickness is 10 μm, whereby a photoreceptor was prepared.

The above-obtained photoreceptor was tested and measured in the samemanner as in Example 1 except that the charging voltage was changed to+6 kv, and the first results were E 1/2=3.1 lux.sec and V_(R) =+5v.

Example 12

An ethylenediamine 2% Exemplified Compound A-7 solution was coated on analuminum-laminated polyester film so that the dry thickness is 0.5 μm,whereby a carrier-generating layer was formed. Further on this wascoated and dried each solution separately prepared by dissolving about10 g each of the foregoing compound T-11, the foregoing compound T-43and the foregoing compound T-184 and 14 g of a polycarbonate resin"Panlite L-1250" (a product of Teijin Chemical Industry Co., Ltd.) toform a layer so that the dry thickness is 12 μm, whereby threephotoreceptors different in the carrier-transport material wereobtained.

These three photoreceptors each was evaluated with respect to thefollowing characteristics with use of an electronic paper tester ModelSP-428, manufactured by Kawaguchi Denki Seisakusho K.K. Eachphotoreceptor was charged for 5 seconds at a charging voltage of -6 kv,then allowed to stand for 5 seconds in the dark, and then exposed to ahalogen lamp light so that the illuminance on the photosensitive surfaceof the sample is 35 luxes, whereby the exposure (half-exposure E 1/2)that is required to reduce the surface potential by half was measured.In addition, the surface potential (residual potential) V_(R) afterbeing subjected to a 30-lux.sec exposure also was measured. The resultswere good in combination with any of the carrier-transport materials asindicated in Table 5.

                  TABLE 5                                                         ______________________________________                                        Carrier-transport material with                                               Exemplified Compound A-7                                                                         E 1/2 (lux.sec)                                                                          V.sub.R (V)                                     ______________________________________                                        T-11               3.2        0                                               T-43               2.5        0                                                T-184             2.6        0                                               ______________________________________                                    

Comparative Example 4

A comparative photoreceptor sample was prepared in the same manner as inExample 11 except that the Exemplified Compound A-101 used in Example 11was replaced by the following bisazo compound C-(4), and then thecharacteristics of the sample were evaluated.

C-(4) ##STR259##

As is indicated in Table 6, the results largely differ between thecarrier-transport materials.

                  TABLE 6                                                         ______________________________________                                        Carrier transport material                                                    with compound C-(4)                                                                             E 1/2 (lux.sec)                                                                          V.sub.R (V)                                      ______________________________________                                        T-11              10.3       40                                               T-43              9.1        25                                                T-184            5.5        10                                               ______________________________________                                    

Example 13

A drum-form photoreceptor was prepared in the same manner as in Example5 except that the Exemplified Compound A-5 used in Example 5 wasreplaced by Excemplified Compound A-194. The spectral sensitivity ofthis photoreceptor at 790 nm was 820 volt.cm².μW⁻¹.sec⁻¹ (lightattenuation rate). The field copying test of the photoreceptor wasperformed using an experimental machine equipped with a semiconductorlaser (790 nm) unit whose laser light intensity on the surface of thephotoreceptor is 0.85 mW.

The surface of the photorecetor was charged at -6 kv, then exposed tothe laser light, and then subjected to reversal development under thecondition of a bias voltage of -250 V, and as a result of fog-free,satisfactory image was obtained.

Comparative Example 5

A comparative photoreceptor sample was prepared in the same manner as inExample 13 except that the Exemplified Compound A-194 used in Example 15was replaced by the following comparative bisazo compound C-(5).

C-(5) ##STR260##

The spectral sensitivity of this photoreceptor at 790 nm was 500volt.cm².μW⁻¹.sec⁻¹ (light attenuation rate). This comparativephotoreceptor was used to perform a field copying test with thesemiconductor laser in like manner, but much fog appeared on theresulting image. Thus, no satisfactory image copies were obtained.

As is apparent from the results from the above examples and comparativeexamples, the photoreceptors of this invention are remarkably excellentin the characteristics such as the stability, sensitivity, durability,permissibility of any combination with diverse carrier-transportmaterials, and the like, as compared to the comparative photoreceptors.

Examples 14 through 27

Drum-form photoreceptor samples were prepared in the same manner as inExample 5 except that the compound T-109 (charge-transport material) wasreplaced as shown in Table 7. The spectral sensitivities of thesephotoreceptor samples at 790 nm are as given in Table 7. As a result ofthe field copying tests in these examples 14-27, which were made in thesame manner as in Example 13, fog-free, satisfactory image copies wereobtained.

                  TABLE 7                                                         ______________________________________                                                                          Spectral                                                                      sensitivity                                                                   (volt ·                            Example Charge-generat-                                                                            Charge-trans-                                                                              cm.sup.2 · μW.sup.-1                                              ·                                  No.     ing material port material                                                                              sec.sup.-1)                                 ______________________________________                                        Example 14                                                                            Exemplified  Compound T-187                                                                             850                                                 compound A-224                                                        Example 15                                                                            Exemplified  Compound T-196                                                                             910                                                 compound A-198                                                        Example 16                                                                            Exemplified  Compound T-126                                                                             900                                                 compound A-222                                                        Example 17                                                                            Exemplified  Compound T-132                                                                             880                                                 compound A-219                                                        Example 18                                                                            Exemplified  Compound T-110                                                                             900                                                 compound A-199                                                        Example 19                                                                            Exemplified  Compound T-122                                                                             850                                                 compound A-115                                                        Example 20                                                                            Exemplified  Compound T-46                                                                              740                                                 compound A-100                                                        Example 21                                                                            Exemplified  Compound T-53                                                                              690                                                 compound A-147                                                        Example 22                                                                            Exemplified  Compound T-155                                                                             860                                                 compound A-128                                                        Example 23                                                                            Exemplified  Compound T-167                                                                             830                                                 compound A-116                                                        Example 24                                                                            Exemplified  Compound T-19                                                                              700                                                 compound A-119                                                        Example 25                                                                            Exemplified  Compound T-244                                                                             690                                                 compound A-234                                                        Example 26                                                                            Exemplified  Compound T-197                                                                             720                                                 compound A-118                                                        Example 27                                                                            Exemplified  Compound T-192                                                                             740                                                 compound A-235                                                        ______________________________________                                    

What is claimed is:
 1. A photoreceptor which have a photosensitive layercontaining an azo compound represented by the following Formula[I],Formula [I] ##STR261## wherein Y₁, Y₂, Y₃ and Y₄ each is a hydrogenatom, an alkyl group, an alkoxy group or a halogen atom; A₁ and A₂ eachrepresents ##STR262## wherein Z is a group of atoms necessary tocomplete a substituted or unsubstituted aromatic carbocyclic ring or asubstituted or unsubstituted aromatic heterocyclic ring; Q₃ is asubstituted or unsubstituted carbamoyl group or a substituted orunsubstituted sulfamoyl group; R₁ is a hydrogen atom, a substituted orunsubstituted alkyl group, a substituted or unsubstituted amino group, asubstituted or unsubstituted carbamoyl group, a carboxyl group or estergroup thereof, or a cyano group; A' is a substituted or unsubstitutedaryl group; and R₂ and R₃ each is a substituted or unsubstituted alkylgroup, a substituted or unsubstituted aralkyl group, or a substituted orunsubstituted aryl group.
 2. The photoreceptor of claim 1, wherein saidphotosensitive layer contains a carrier-generating material and acarrier-transport material, and said carrier-generating material is saidazo compound.
 3. The photoreceptor of claim 2, wherein saidphotosensitive layer consists of a carrier-generating layer containingsaid carrier-generating material and a carrier-transport layercontaining said carrier-transport material.
 4. The photoreceptor ofclaim 1, wherein said azo compound is represented by the followingFormula [II],Formula [II] ##STR263## wherein Y₁, Y₂, Y₃ and Y₄ are thesame as those of claim 1, R₆, R₇, R₈, R₉ and R₁₀ are a hydrogen atom, ahalogen atom, an aryl group, an alkyl group or an alkoxy group,independently.
 5. The photoreceptor of claim 1, wherein said azocompound is represented by the following Formula [III],Formula [III]##STR264## wherein Y₁, Y₂, Y₃ and Y₄ are the same as those of claim 1,and R₆, R₇, R₈, R₉ and R₁₀ are a hydrogen atom, a halogen atom, an arylgroup, an alkyl group or an alkoxy group, independently.
 6. Thephotoreceptor of claim 1, wherein said azo compound is represented bythe following Formula [IV],Formula [IV] ##STR265## wherein Y₁, Y₂, Y₃and Y₄ are the same as those of claim 1, and R₆, R₇, R₈, R₉ and R₁₀ area hydrogen atom, a halogen atom, an aryl group, an alkyl group or analkoxy group, independently.
 7. The photoreceptor of claim 1, whereinsaid azo compound is represented by the following Formula [V],Formula[V] ##STR266## wherein Y₁, Y₂, Y₃ and Y₄ are the same as those of claim1, and R₆, R₇, R₈, R₉ and R₁₀ are a hydrogen atom, a halogen atom, anaryl group, an alkyl group or an alkoxy group, independently.
 8. Thephotoreceptor of claim 1, wherein said azo compound is represented bythe following Formula [VI],Formula [VI] ##STR267## wherein Y₄ is thesame as that of claim 1, R₆, R₇, R₈, R₉ and R₁₀ are a hydrogen atom, ahalogen atom, an aryl group, an alkyl group or an alkoxy group,independently; and R₁₁, R₁₂, R₁₃, R₁₄ and R₁₅ are a hydrogen atom, ahalogen atom, an alkyl group or an alkoxy group, independently.
 9. Thephotoreceptor of claim 1, wherein said azo compound is represented bythe following Formula [VII],Formula [VII] ##STR268## wherein Y is thesame as that of claim 1, R₆, R₇, R₈, R₉ and R₁₀ are a hydrogen atom, ahalogen atom, an aryl group, an alkyl group or an alkoxy group,independently; and R₁₁, R₁₂, R₁₃, R₁₄ and R₁₅ are a hydrogen atom, ahalogen atom, an alkyl group or an alkoxy group, independently.
 10. Thephotoreceptor of claim 2, wherein said carrier-transport material isselected from the group consisting of trinitrofluorenone,tetranitrofluorenone, polymers having in the side chain thereofheterocyclic compounds typified by poly-N-vinylcarbazole, triazolederivatives, oxadiazole derivatives, imidazole derivatives, pyrazolinederivatives, polyarylalcane derivatives, phenylendiamine derivatives,hydrazone derivatives, amino-substituted chalcone derivatives,triarylamine derivatives, carbazole derivatives, stilbene derivatives,and phenothiazine derivatives.
 11. The photoreceptor of claim 10,wherein said carrier-transport material is represented by the followingFormula [VIII],Formula [VIII] ##STR269## wherein R₁₆, R₁₇ and R₁₈ eachis a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, ahydroxy group, a cyano group, a dialkylamino group, a diarylamino group,a diaralkylamino group, or a nitro group.
 12. The photoreceptor of claim10, wherein said carrier-transport material is represented by thefollowing Formula [IX],Formula IX] ##STR270## wherein R₁₉, R₂₂, R₂₃, R₂₄and R₂₅ each is a hydrogen atom, an alkyl group, an alkoxy group, ahalogen atom, a hydroxy group, a cyano group, a dialkylamino group, adiarylamino group, a diaralkylamino group or a nitro group; R₂₀ is analkyl group, a substitutable phenyl group, a substitutable benzyl group,or a substitutable naphthyl group; and R₂₁ is a hydrogen atom, an alkylgroup, a cyano group or a substitutable phenyl group.
 13. Thephotoreceptor of claim 10, wherein said carrier-transport material isrepresented by the following Formula [X],Formula [X] ##STR271## whereinR₂₆, R₂₇, R₂₈ and R₂₉ is a hydrogen atom, an alkyl group, an alkoxygroup, a halogen atom, a hydroxy group, a cyano group, a dialkylaminogroup, a diarylamino group, a diaralkylamino group or a nitro group; R₃₀is a hydrogen atom, a substitutable phenyl group, a cyano group or analkyl group; Ar is ##STR272## wherein R₃₁, R₃₂ and R₃₃ each is an alkylgroup, a substitutable benzyl group, a substitutable phenyl group or asubstitutable naphthyl group; and R₃₄ is a hydrogen atom, an alkylgroup, an alkoxy group, a halogen atom, a hydroxy group, a cyano group,a dialkylamino group, a diarylamino group, diaralkylamino group, or anitro group.
 14. The photoreceptor of claim 10, wherein saidcarrier-transport material is represented by the following Formula[XI],Formula [XI] ##STR273## wherein R₃₅, R₃₆, R₃₇ and R₃₈ each is ahydrogen atom, an alkyl group, an alkoxy group, a halogen atom, ahydroxy group, a cyano group, a dialkylamino group, a diarylamino group,a diaralkylamino group, or a nitro group; R₃₉ is a hydrogen atom, asubstitutable phenyl group, a cyano group, or an alkyl group; Ar is##STR274## wherein R₄₀, R₄₁ and R₄₂ each is an alkyl group, asubstitutable benzyl group, a substitutable phenyl group, or asubstitutable naphthyl group; and R₄₃ is a hydrogen atom, an alkylgroup, an alkoxy group, a halogen atom, a hydroxy group, a cyano group,a dialkylamino group, a diarylamino group, a diaralkylamino group, or anitro group.
 15. The photoreceptor of claim 10, wherein saidcarrier-transport material is represented by the following Formula[XII],Formula [XII] ##STR275## wherein R₄₄, R₄₅ and R₄₆ each is ahydrogen atom, an alkyl group, an alkoxy group, a halogen atom, ahydroxy group, a cyano group, a dialkylamino group, a diarylamino group,a diaralkylamino group, or a nitro group; and n is an integer of zeroor
 1. 16. The photoreceptor of claim 10, wherein said carrier-transportmaterial is represented by the following Formula [XIII],Formula [XIII]##STR276## wherein R₄₇, R₄₈, R₄₉, R₅₀, R₅₁ and R₅₂ each is a hydrogenatom, an alkyl group, an alkoxy group, a halogen atom, a hydroxy group,a cyano group, a dialkylamino group, a diarylamino group, adiaralkylamino group, or a nitro group; and R₇ is a hydrogen atom or aphenyl group.
 17. The photoreceptor of claim 10, wherein saidcarrier-transport material is represented by the following Formula[XIV],Formula [XIV] ##STR277## wherein R₅₄, R₅₅, R₅₆, R₅₇, R₅₈ and R₅₉each is a hydrogen atom, an alkyl group, an alkoxy group, a halogenatom, a hydroxy group, a cyano group, a dialkylamino group, adiarylamino group, a diaralkylamino group, or a nitro group; and R₆₀ isa hydrogen atom or a phenyl group.
 18. The photoreceptor of claim 10,wherein said carrier-transport material is represented by the followingFormula [XV],Formula [XV] ##STR278## wherein R₆₁, R₆₂, R₆₃, R₆₄, R₆₅ andR₆₆ each is a hydrogen atom, an alkyl group, an alkoxy group, a halogenatom, a hydroxy group, a cyano group, dialkylamino group, diarylaminogroup, a diaralkylamino group, or a nitro group.
 19. The photoreceptorof claim 3, wherein said carrier-generating layer has the thickness inthe range of from 0.01 μm to 5 μm.
 20. The photoreceptor of claim 2,wherein said photosensitive layer is a single layer which contains saidcarrier-transport material and said carrier-generating material eachdispersed therein.